Electric Literature of 53312-79-1, These common heterocyclic compound, 53312-79-1, name is 3-Amino-4-chlorobenzonitrile, 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.
(1) 4-Chloro-3-(1-nitro-2-naphthylamino)benzonitrile A suspension of 1-nitro-2-naphthyltriflate (1.50 g, 4.67 mmol), 3-amino-4-chlorobenzonitrile (1.05 g, 6.87 mmol), potassium carbonate (645 mg, 4.67 mmol), tetrakis(triphenylphosphine)palladium(0) (162 mg, 0.14 mmol) and triphenylphosphine (65 mg, 0.47 mmol) in toluene (45 mL) was stirred at 110C for 16 hours. The reaction mixture was cooled to room temperature, and filtered. The filtrate was diluted with chloroform, washed with 0.2M hydrochloric acid, a saturated aqueous sodium bicarbonate solution and saturated brine. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate = 1/1), to give the titled compound (900 mg, yield 60%). 1H-NMR(CDCl3, 400MHz) delta: 7.31(1H, dd, J=2, 8Hz), 7.44(1H, d, J=9Hz), 7.52(1H, t, J=8Hz), 7.58(1H d, J=8Hz), 7.62(1H, d, J=1Hz), 7.68(1H, m), 7.84(1H, d, J=8Hz), 7.96(1H, d, J=9Hz), 8.25(1H, d, J=9Hz), 8.67(1H, br s).
Statistics shows that 3-Amino-4-chlorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 53312-79-1.
Reference:
Patent; Nippon Chemiphar Co., Ltd.; EP2397480; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts