Application of 51762-67-5, A common heterocyclic compound, 51762-67-5, name is 3-Nitrophthalonitrile, molecular formula is C8H3N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
The synthetic procedure was adopted from Mayukh etal. with some modifications [37]. A mixture of 4-mercaptophenol (1.26g, 0.01mol) and K2CO3 (4.15g, 0.03mol) in dry dimethylformamide (DMF) (25mL) was stirred vigorously in nitrogen atmosphere for 30min and then 3-nitrophthalonitrile (1.75g, 0.01mol) was added into the reaction mixture followed by a stirring for 16h at 90C. The reaction mixture was allowed to cool room temperature and poured into 1M HCl and the precipitate formed was filtered off and washed with water until the filtrate was neutral and dried in vacuum. The precipitate was extracted with ethyl acetate. The combined organic phases were treated with distilled water, dried with anhydrous sodium sulfate and solvent removed under reduced pressure to obtain solid orange colored powder. The product was further purified by chromatography over a silica gel column using Ethyl acetate and hexane (3:1) mixture as eluent. Yield: 1.73g, (68%); m.p. 162-164C. FT-IR numax/cm-1; 3403 (Ar-OH), 3077-2923 (Ar-H), 2241 (C?N). 1H NMR (DMSO-d6) delta/ppm: 10.18 (s, 1H, Ar-OH), 7.84 (d, 1H, Ar-H), 7.68 (t, 1H Ar-H), 7.42 (d, 2H, Ar-H), 7.09 (d, 1H, Ar-H), 6.91ppm (d, 2H, Ar-H); 13C NMR (DMSO-d6) delta/ppm: 160.21 (aromatic C-O), 147.51, 137.76, 134.51, 130.96, 117.97, 116.40 (C?N), 114.57, 110.27. Anal. Calcd. for C14H8N2OS (252.291g/mol); C 66.65, H 3.20, N 11.10; Found: C 66.56, H 3.09, N 11.08. MS (GC/MS): m/z: 252 [M]+.
The synthetic route of 51762-67-5 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Suerguen, Serdar; Arslano?lu, Yasin; Hamuryudan, Esin; Dyes and Pigments; vol. 100; 1; (2014); p. 32 – 40;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts