untitled European Journal of Chemistry 4 (1) (2013) 53‐57 European Journal of Chemistry ISSN 2153‐2249 (Print) / ISSN 2153‐2257 (Online)  2013 EURJCHEM DOI:10.5155/eurjchem.4.1.53‐57.733 European Journal of Chemistry Journal homepage: www.eurjchem.com An efficient route for the synthesis of some monoazo disperse dyes derived from nicotinic acid derivatives Abdulaziz Alnajjar a, Marzouq Alsaiedi a and Morsy Ahmed El‐Apasery b,* a Applied Science Department, College of Technological Studies, Public Authority for Applied Education and Training, Safat, 70654, Kuwait b Dyeing, Printing and Textile Auxiliaries Department, Textile Research Division, National Research Centre, 12622 Dokki, Giza, Egypt *Corresponding author at: Dyeing, Printing and Textile Auxiliaries Department, Textile Research Division, National Research Centre, 12622 Dokki, Giza, Egypt. Tel.: +2.02.3371718; fax: +2.02.3370931. E‐mail address: elapaserym@yahoo.com (M.A. El‐Apasery). ARTICLE INFORMATION ABSTRACT Received: 03 January 2013 Received in revised form: 04 February 2013 Accepted: 05 February 2013 Online: 31 March 2013 KEYWORDS Ethyl 2‐amino‐3‐cyano‐4‐phenylnicotinates (8), could be readily synthesized via reacting ethyl propiolate with benzylidenemalononitrile in the presence of L‐proline as a catalyst and subsequent rearrangement of the so formed 2‐aminopyran (7), with acetic acid in the presence of ammonium acetate. A series of 2‐amino and 2‐hydroxyarylazonicotinates monoazo disperse dyes (12a‐c), were prepared in a good yields via condensation of arylhydrazonals (11a‐c), with active methylene nitriles. The compound 9 was also characterized by single crystal X‐ray diffraction studies. Crystal data for compound 9, C15H18O6 (M = 294.29): hexagonal, space group P65 (no. 170), a = 11.3311(5) Å, c = 19.5375(10) Å, V = 2172.42(18) Å3, Z = 6, T = 296(2) K, μ(MoKα) = 0.879 mm‐1, Dcalc = 1.350 g/mm3, 4546 reflections measured (9.02 ≤ 2Θ ≤ 132.96), 2271 unique (Rint = 0.0921) which were used in all calculations. The final R1 was 0.0686 (>2σ(I)) and wR2 was 0.1691 (all data). Enaminones Nicotinic acid Disperse dyes Arylhydrazonals Dye intermediates Arylazonicotinates 1. Introduction Every year, a number of dyes are introduced for coloring textile fibres by researchers and colorists. Only a few of those are commercialized, after passing necessary standards such as good build up, fastness properties and toxicity [1]. It is well known that disperse dyes are the most important group for dyeing of hydrophobic fibres, especially polyester. The considerable biological and medicinal activities of nicotinic acid and its derivatives [2‐5] have promoted recent interest in synthesis of new nicotinic acids of potential biological activities. Although condensation reactions of arylhydrazonals with active methylene nitriles were originally reported to afford pyridazin‐6‐imines [6], more recent studies have demonstrated that arylazonicotinates are also formed in some of these processes [7‐9]. Because arylazonicotinates are a valuable class of arylazopyridine dyes whose chemistry has attracted some interest as new disperse dyes [10‐12], it seemed of value to undertake an investigation aimed at exploring the potential utility of arylhydrazonals as precursors for the preparation of these targets. In conjunction to our effort for synthesis poly‐substituted nicotinates either as new antimicrobial agents or new disperse dye intermediates, we report herein, synthesis of new potential antimicrobial and disperse dyes with nicotinic acid skeleton via simple efficient routes. Also our investigation, described below, has led to the synthesis of different types of substances, including 2‐aminoazonicotinate and 2‐hydroxyazonicotate derivatives for utilizing as heterocyclic components for various disperse dyes. 2. Experimental 2.1. Instrumentation Melting points are uncorrected. All melting points were recorded on a Griffin melting point apparatus and are reported uncorrected. IR spectra were recorded using KBr disks using a Perkin‐Elmer System 2000 FT‐IR spectrophotometer. 1H NMR (400 MHz) or (600 MHz) and 13C NMR (100 MHz) or (150 MHz) spectra were recorded at 25 °C in CDCl3 or DMSO‐d6 as solvent with TMS as internal standard on a Bruker DPX 400 or 600 super‐conducting NMR spectrometer. Chemical shifts are reported in ppm. Mass spectra were measured using a high resolution GC‐MS (DFS) Thermo spectrometer with EI (70 EV). Microanalyses were performed on a LECO CHNS‐932 Elemental Analyzer. Compounds 10b, 10c, and 11b are prepared according to our previous work [13,14]. The crystal structure of compound 9 was determined by Bruker AXS X8 Prospector Single Crystal X‐Ray Diffractometer at Kuwait University. The crystal was kept at 296(2) K during data collection. The structure was solved with the Program SHELXL‐97 Software package. 2.2. Ethyl‐6‐amino‐5‐cyano‐4‐phenyl‐4H‐pyran‐3‐ carboxylate (7) A mixture of benzylidene malononitrile, 1a, (1.54 g, 0.01 mol), ethyl propiolate, 2, (1.0 g, 0.01 mol) and L‐proline, 3, (10% mol) was added together. The mixture was refluxed in absolute ethanol (15 mL) for 4 h, followed by TLC. The crude compound formed was recrystallized from ethanol as white crystalline solid (Scheme 1). Yield: 65%. M.p.: 227‐230 °C. 1H NMR (400 MHz, DMSO‐d6, δ, ppm): 1.08 (t, 3H, J = 7.2 Hz, CH3), 4.01 (q, 2H, J = 7.2 Hz, CH2), 4.23 (s, 1H, pyran H4), 7.03 (s, 2H, NH2), 7.17 (d, 2H, J = 8.0 Hz, Ar‐H), 7.23 (t, 1H, J = 8.0 Hz, Ar‐H), 7.32 (t, 2H, J = 8.0 Hz, Ar‐H), 7.71 (s, 1H, pyran H6). 54 Alnajjar et al. / European Journal of Chemistry 4 (1) (2013) 53‐57 Scheme 1 13C NMR (100 MHz, DMSO‐d6, δ, ppm): 14.33 (CH3), 37.55 (pyran C4), 57.79 (pyran C3), 60.70 (CH2), 111.78 (pyran C5), 120.16 (CN), 127.41, 127.84, 128.93, 144.69, 148.23, 159.05 (CO), 164.98 (pyran C6). MS (m/z, (%)): 270 (M+, 43), 271 (M++1, 8). Anal. calcd. for C15H14N2O3: C, 66.66; H, 5.22; N, 10.36. Found: C, 66.58; H, 5.29; N, 10.44%. 2.3. Ethyl‐6‐amino‐5‐cyano‐4‐phenylnicotinate (8) A solution of pyran, 7, (0.70 g, 2.5 mmol) in acetic acid (10 mL) containing ammonium acetate (1 g) was refluxed 5 h, Then, the reaction mixture was cooled to room temperature. The solid which formed was collected by filtration, washed with water and recrystallized from ethanol as yellowish white crystalline solid (Scheme 1). Yield: 71%. M.p.: 179‐181 °C. 1H NMR (400 MHz, DMSO‐d6, δ, ppm): 0.87 (t, 3H, J = 7.2 Hz, CH3), 3.92 (q, 2H, J = 7.2 Hz, CH2), 7.28‐7.30 (m, 2H, Ar‐H), 7.45‐7.47 (m, 3H, Ar‐H), 7.7 (s, 2H, NH2), 8.67 ppm (s, 1H, pyridyl H6). 13C NMR (100 MHz, DMSO‐d6, δ, ppm): 13.46 (CH3), 60.17 (CH2), 90.53 (pyridyl C3), 114.41 (pyridyl C5), 115.48 (CN), 127.72, 128.01, 128.61, 136.78, 155.02, 156.25, 161.66 (CO), 164.52 (pyridyl C6). MS (m/z, (%)): 267 (M+, 44), 268 (M++1, 9). Anal. calcd. for C15H13N3O2: C, 67.41; H, 4.90; N, 15.72. Found: C, 67.54; H, 4.83; N, 15.81%. 2.4. Benzen ‐1,3,5‐tricarboxylic acid triethyl ester (9) A mixture of p‐chlorobenzylidene malononitrile, 1b, (1.54 g, 0.01 mol), ethyl propiolate (1.0 g, 0.01 mol) and L‐proline or DBU (10% mol) was added together. The mixture was refluxed in absolute ethanol (15 mL) for 8 h, followed by TLC. The crude compound formed was recrystallized from ethanol as pale yellow crystalline solid (Scheme 1). Yield: 81%. M.p.: 140‐142 °C. 1H NMR (400 MHz, DMSO‐d6, δ, ppm): 1.38 (t, 9H, J = 7.2 Hz, 3CH3), 4.41 (q, 6H, J = 7.2 Hz, 3CH2), 8.65 (s, 3H, Ar‐H). MS (m/z, (%)): 294 (M+, 11), 295 (M++1, 5.). Anal. calcd. for C15H18O6: C, 61.22; H, 6.16. Found: C, 61.29; H, 6.19%. 2.5. 3‐Dimethylamino‐1‐naphthalen‐2‐yl‐propenone (10a) A mixtures of 2‐acetylnaphthalen (10 mmol) and N,N‐ dimethylformamide‐dimethylacetal (DMF‐DMA) (15 mmol) were stirred at reflux for 24 h. The separated solid product obtained on standing at room temperature was collected by filtration, washed by EtOH and recrystallized from EtOH to afford the corresponding enaminone, 10a, as yellow crystals (Scheme 2). Yield: 85%. M.p.: 92‐94 °C. FT‐IR (KBr cm‐1): 1639 (CO). 1H NMR (400 MHz, DMSO‐d6, δ, ppm): 2.88 (s, 3H, CH3), 3.11 (s, 3H, CH3), 5.84 (d, 1H, J =12 Hz, olefinic CH), 7.41‐7.50 (m, 3H, Ar‐H), 7.76 (d, 1H, J = 12 Hz, olefinic CH), 7.91‐7.93 (m, 4H, Ar‐H). MS (m/z, (%)): 225 (M+, 66), 226 (M++1, 8). Anal. calcd. for C15H15NO: C, 79.97; H, 6.71; N, 6.22. Found: C, 80.05; H, 6.77; N, 6.18%. 2.6. General procedure for the preparation of compounds (11a,c) Cold solution of benzenediazonium chloride (10 mmol) was prepared by adding a solution of sodium nitrite (1.4 g dissolved in 10 mL water) to cold solution of primary aromatic amines hydrochloride (10 mmol in 10 mL, 6 M HCl) with stirring. The resulting solution of benzenediazonium chloride was then added to a cold solution of the enaminones, 10a or 10c, (10 mmol) in ethanol (50 mL) in the presence of sodium acetate (4.2 g, 30 mmol). Alnajjar et al. / European Journal of Chemistry 4 (1) (2013) 53‐57 55 Scheme 2 Scheme 3 The reaction mixture was stirred at room temperature for 1 h. The formed solid product was collected by filtration and washed with water then recrystallized from EtOH to afford compound 11a or 11c, respectively. 2‐[(4‐Chlorophenyl)hydrazono]‐3‐naphthalen‐2‐yl‐3‐ oxopropionaldehyde (11a): Yellow crystals (Scheme 2). Yield: 74%. M.p.: 128‐130 °C. FT‐IR (KBr cm‐1): 3431 (NH), 1637 (CO). 1H NMR (400 MHz, DMSO‐d6, δ, ppm): 7.41‐7.52 (m, 4H, Ar‐H), 7.62‐7.73 (m, 2H, Ar‐H), 7.92‐8.54 (m, 5H, Ar‐H), 10.06 (s, 1H, NH), 14.16 (s, 1H, CHO). MS (m/z, (%)): 336 (M+, 38), 337 (M++1, 7.75). Anal. calcd. for C19H13ClN2O2: C, 67.76; H, 3.89; N, 8.32.Found: C, 67.71; H, 3.95; N, 8.44%. 3‐Oxo‐3‐(pyrazin‐2‐yl)‐2‐(2‐p‐tolylhydrazono)propanal (11c): Wine red crystals (Scheme 3). Yield: 78%. M.p.: 140‐141 °C. FT‐IR (KBr cm‐1): 3119 (NH), 1657, 1642 (CO). 1H NMR (400 MHz, DMSO‐d6, δ, ppm): 2.28 (s, 3H, CH3), 7.20 (d, 2H, J = 6.8 Hz, Ar‐H), 7.29 (d, 2H, J = 5.6 Hz, Ar‐H), 8.81‐8.85 (m, 2H, Ar‐H), 9.04 (s, 1H, Ar‐H); 10.02 (s, 1H, NH), 14.36 (s, 1H, CHO). 13C NMR (100 MHz, DMSO‐d6, δ, ppm): 20.8 (CH3), 117.0, 130.0, 131.7, 136.3, 138.9, 143.7, 144.7, 145.0, 150.8, 187.0, 188.7. MS (m/z, (%)): 268 ([M]+, 20). Anal. calcd. for C14H12N4O2: C, 62.68; H, 4.51; N, 20.88;. Found: C, 62.88; H, 4.82; N, 20.57%. 2.7. Ethyl 2‐amino‐5‐((4‐chlorophenyl)diazenyl)‐6‐ (naphthalen‐2‐yl)nicotinate (12a) A mixture of the arylhydrazonalas, 11a, (10 mmol), ethyl cyanoacetate (1.2 g, 10 mmol) and ammonium acetate (2 g) in acetic acid (30 mL) was refluxed for 2 h. then allowed to cool down to room temperature and poured onto ice cold water. The formed precipitate was collected by filtration washed with water and recrystallized from ethanol as orange crystals (Scheme 2). Yield: 77%. M.p.: 89‐90 °C. FT‐IR (KBr cm‐1): 3444, 4350 (NH2), 1743 (CO). 1H NMR (400 MHz, DMSO‐d6, δ, ppm): 1.37 (t, 3H, J = 7.4 Hz, CH3), 4.39 (q, 2H, J = 7.4 Hz, CH2), 7.56‐ 7.62 (m, 4H, Ar‐H), 7.72 (d, 2H, J = 8.0 Hz, Ar‐H), 7.93‐8.02 (m, 4H, Ar‐H), 8.12 (br, 2H, NH2), 8.35 (s, 1H, Ar‐H), 8.62 (s, 1H, pyridine H). 13C NMR (100 MHz, DMSO‐d6, δ, ppm): 14.2 (CH3), 61.2 (CH2), 105.1, 124.0, 126.5, 126.6, 127.2, 127.4, 127.5, 128.2, 128.6, 129.4, 129.5, 131.0, 132.2, 133.1, 134.6, 134.9, 136.6, 150.9, 159.8, 166.2 (CO). MS (m/z, (%)): 430 (M+, 100), 431 (M++1, 55). Anal. calcd. for C24H19ClN4O2: C, 66.90; H, 4.44; N, 13.00. Found: C, 66.88; H, 4.38; N, 13.11%. 2.8. General procedure for the synthesis of compounds (12b,c and 14) Independent mixtures of compound 11b or 11c (0.01 mol), ethyl cyanoacetate or cyanoacetamide (0.01 mol), and ammonium acetate (0.5 g) in acetic acid (10 mL) was stirred at reflux for 30 min (progress of the reactions was monitored by using TLC using ethyl acetate: petroleum ether (1:1). The mixtures were cooled and then poured into ice‐water. The solids that formed were collected by using filtration and crystallized from ethanol to give compound 12b,c and 14. Ethyl 2‐hydroxy‐5‐(phenyldiazenyl)‐6‐(1H‐pyrrol‐2‐yl)‐ nicotinate (12b): Dark brown powder (Scheme 3). Yield: 60%. M.p.: 202‐204 °C. FT‐IR (KBr cm‐1): 3300 (OH), 3064 (NH), 1598 (CO). 1H NMR (400 MHz, DMSO‐d6, δ, ppm): 1.30 (t, 3H, J = 7.2 Hz, CH3), 4.31 (q, 2H, J = 7.2 Hz, CH2), 7.10‐7.77 (m, 8H, Ar‐ H), 8.31 (s, 1H, pyridyl‐H); 11.89 (s, 1H, NH, D2O exchangeable)., 12.18 (s, 1H, OH, D2O exchangeable). 13C NMR (100 MHz, DMSO‐d6, δ, ppm): 13.9 (CH3), 61.7 (CH2), 110.9, 117.2, 121.2, 123.0, 126.0, 127.5, 128.8, 129.0, 130.9, 131.4, 141.3, 141.8, 175.0, 176.9 (CO). MS (m/z, (%)): 337 ([M+1]+, 95). Anal. calcd. for C18H16N4O3: C, 64.28; H, 4.79; N, 16.66. Found: C, 63.97; H, 4.63; N, 16.44%. HRMS: m/z (EI) for C18H16N4O3; calcd. 336.1216; found: 336.1216. Ethyl 2‐hydroxy‐6‐(pyrazin‐2‐yl)‐5‐(p‐tolyldiazenyl)‐ nicotinate (12c): Dark red powder (Scheme 3). Yield: 68%. M.p.: >300 °C. FT‐IR (KBr cm‐1): 3312 (OH), 1610 (CO). 1H NMR (400 MHz, DMSO‐d6, δ, ppm): 1.30 (t, 3H, J = 7.2 Hz, CH3), 2.33 (s, 3H, CH3), 4.23 (q, 2H, J = 7.2 Hz, CH2), 7.06‐7.77 (m, 6H, Ar‐ H), 8.16 (s, 1H, Ar‐H), 9.04 (s, 1H, arom‐H), 12.00 (s, 1H, OH, D2O exchangeable). 13C NMR (100 MHz, DMSO‐d6, δ, ppm): 13.9 (CH3), 20.7 (CH3), 55.8 (CH2), 112.6, 117.1, 121.3, 123.2, 125.6, 127.5, 128.8, 129.2, 132.4, 135.0, 139.9, 157.5, 161.9, 165.7 (CO). 56 Alnajjar et al. / European Journal of Chemistry 4 (1) (2013) 53‐57 Scheme 4 Figure 1. X‐ray crystal structure of compound 9. MS (m/z, (%)):363 (M+). Anal. calcd. for C19H17N5O3: C, 62.80; H, 4.72; N, 19.27. Found: C, 62.55; H, 4.65; N, 19.16 %. 3‐Oxo‐2‐phenyl‐6‐(1H‐pyrrole‐5‐carbonyl)‐2,3‐dihydro pyridazine‐4‐carboxamide (14): Brown powder (Scheme 4). Yield: 88%. M.p.: 250‐252 °C. FT‐IR (KBr cm‐1): 3372, 3301 (NH2), 3063 (NH), 1697 (CO), 1595 (CO). 1H NMR (400 MHz, DMSO‐d6, δ, ppm): 6.25 (s, 1H, Ar‐H), 7.09‐7.66 (m, 4H, Ar‐H), 7.68 (d, 2H, J = 8.0 Hz Ar‐H), 7.76 (d, 1H, J = 8.4 Hz Ar‐H), 8.59 (s, 1H, pyridazinyl‐H), 11.90 (s, 1H, NH), 12.22 (s, 2H, NH2, D2O exchangeable). 13C NMR (100 MHz, DMSO‐d6, δ, ppm): 110.66, 117.2, 118.8, 121.3, 126.1, 127.6, 129.0, 131.8, 141.3, 149.5, 159.5, 162.2, 175.1, 176.9. MS (m/z, (%)): 308 ([M]+, 100). Anal. calcd. for C16H12N4O3: 62.33; H, 3.92; N, 18.17. Found: 62.41; H, 4.19; N, 18.32%. HRMS: m/z (EI) for C16H12N4O3; calcd. 308.0904; found: 308.0904. 3. Results and discussion Similar to recent report [15], ethyl propiolate (2), and benzylidenemalononitrile (1), reacted in ethanolic solution in the presence of catalytic amount of L‐proline, as a catalyst, yielded the 2‐aminopyran, 7, in 65 % yield. It is believed that compound 2 initially add L‐proline to yield compound 4 that then reacted with benzylidenemalononitrile yielding the acyclic intermediate, 5, that then afford compound 6 that cyclized into the pyran, 7. The 2‐aminopyran, 7, readily rearranged into the 2‐aminonicotinate, 8, when refluxed in acetic acid in the presence of ammonium acetate (Scheme 1). Thus trials to extend this approach for synthesis of other substituted nicotinates, 8, via reacting compound 1b with compound 2 utilizing the same procedure failed. As instead of formation of compound 7b the 1,3,5‐trisubstituted benzoate, 9, was formed and whose structure could be confirmed by the X‐ ray crystal structure determination (Figure 1). Crystal data and structure refinement for compound 9 are listed in Table 1. Bond distances and angles calculated from the final atomic coordinates are given in Table 2 and 3, respectively. Table 1. Crystal data and structure refinement for compound 9. Empirical formula C15H18O6 Formula weight 294.29 Temperature/K 296(2) Crystal system Hexagonal Space group P65 a/Å 11.3311(5) b/Å 11.3311(5) c/Å 19.5375(10) α/° 90 β/° 90 γ/° 120 Volume/Å3 2172.42(18) Z 6 ρcalc mg/mm3 1.350 m/mm‐1 0.879 F(000) 936.0 Crystal size/mm3 0.34 × 0.07 × 0.04 2Θ range for data collection 9.02 to 132.96° Index ranges ‐12 ≤ h ≤ 10, ‐10 ≤ k ≤ 12, ‐23 ≤ l ≤ 21 Reflections collected 4546 Independent reflections 2271[R(int) = 0.0921] Data/restraints/parameters 2271/1/193 Goodness‐of‐fit on F2 1.064 Final R indexes [I>=2σ (I)] R1 = 0.0686, wR2 = 0.1650 Final R indexes [all data] R1 = 0.0779, wR2 = 0.1691 Largest diff. peak/hole / e Å‐3 0.41/‐0.38 Flack parameter ‐0.1(3) In an alternative synthetic methodology ethyl 2‐amino‐ or ethyl 2‐hydroxyazonicotinate disperse dyes, 12a‐c, could be synthesized. Thus compounds 10a‐c coupled with aryldiene diazonium chloride to yield compounds 11a‐c. Compound 11a condensed with ethyl cyanoacetate to yield ethyl 2‐ aminoazonicotinate disperse dye, 12a (Scheme 2). Alnajjar et al. / European Journal of Chemistry 4 (1) (2013) 53‐57 57 Table 2. Bond lengths for compound 9. Atom Atom Length, Å Atom Atom Length, Å O1 C2 1.456(3) C4 C5 1.394(4) O1 C3 1.336(3) C4 C14 1.385(4) O2 C7 1.338(3) C5 C6 1.392(4) O2 C8 1.457(3) C6 C7 1.499(4) O3 C11 1.458(3) C6 C15 1.383(4) O3 C12 1.339(3) C8 C9 1.495(4) O4 C12 1.206(4) C10 C11 1.499(4) O5 C3 1.205(3) C12 C13 1.495(4) O6 C7 1.208(3) C13 C14 1.395(4) C1 C2 1.488(4) C13 C15 1.390(4) C3 C4 1.497(4) Table 3. Bond angles for compound 9. Atom Atom Atom Angle, ˚ Atom Atom Atom Angle, ˚ C3 O1 C2 116.1(2) O2 C7 C6 111.9(2) C7 O2 C8 116.8(2) O6 C7 O2 124.0(3) C12 O3 C11 115.9(2) O6 C7 C6 124.1(3) O1 C2 C1 107.3(2) O2 C8 C9 107.2(2) O1 C3 C4 111.6(2) O3 C11 C10 107.3(3) O5 C3 O1 124.5(3) O3 C12 C13 111.9(2) O5 C3 C4 123.9(3) O4 C12 O3 124.3(2) C5 C4 C3 118.3(2) O4 C12 C13 123.8(3) C14 C4 C3 121.7(2) C14 C13 C12 117.9(2) C14 C4 C5 120.0(2) C15 C13 C12 122.8(3) C6 C5 C4 119.7(3) C15 C13 C14 119.4(3) C5 C6 C7 121.4(3) C4 C14 C13 120.4(2) C15 C6 C5 120.2(3) C6 C15 C13 120.4(2) C15 C6 C7 118.4(2) In contrast, when the condensation reaction of compound 11b or 11c with ethyl cyanoacetate are conducted in the presence of a catalytic amount of ammonium acetate, ethyl 2‐ hydroxyazonicotinate, 12b or 12c, disperse dyes are produced (Scheme 3). In the final phase of the current effort, we observed that reactions of compound 11b with cyanoacetamide in the presence of ammonium acetate in acetic acid for one hour lead to the respective pyridazinone, 14, which is likely formed via the intermediacy of the readily hydrolyzed imine analogs, 13 (Scheme 4). Currently, we are utilizing the 2‐amino‐ and 2‐ hydroxyl‐ azonicotinates disperse dyes for dyeing polyester fabrics by using high temperature dyeing method. We are also inspecting the biological activity of these disperse dyes against Gram‐ positive bacteria, Gram‐negative bacteria and yeast 4. Conclusion In conclusion, in the investigation described above, a series of arylazonicotinates disperse dyes were synthesized in a good yields via condensation of arylhydrazonals with active methylenes. Acknowledgements This research was done by the financial support of the Public Authority for Applied Education and Training (Transform grant TS‐07‐11) of Kuwait. 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