Reference of 38487-86-4, These common heterocyclic compound, 38487-86-4, name is 2-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.
2-Amino-4-chlorobenzonitrile (4) (305 mg, 2 mmol)was dissolved in 94% H2SO4 (2 ml) at 20-25. Theobtained nitrile solution was cooled (5-10), stirred, andtreated by slow dropwise addition of 1-(3-bromo-4-methoxyphenyl)-2-methylpropan-1-ol (10) (518 mg, 2 mmol) asa solution in H2Cl2 (0.5 ml). The reaction mixture wasstirred for 1 h at 20-25 and further treated according tothe general method. The product was crystallized fromEtOAc, the residue was separated by chromatography (eluentpetroleum ether – EtOAc, gradient from 10:1 to 1:1). Yield90 mg (12%, general method), 420 mg (56%, method II),light-yellow crystals, mp 245.5-247, Rf 0.20 (hexane-EtOAc, 4:1). IR spectrum, nu, cm-1: 1610, 1683, 3321.1H NMR spectrum, delta, ppm (J, Hz): 1.31 (3, s, 2-3);1.36 (3, s, 2-3); 2.03 (1, d, J = 13.2, 3-2); 2.20(1, d, J = 13.2, 3-2); 2.76 (1, dd, J = 16.8, J = 3.2,7-2); 3.02 (1, dd, J = 16.8, J = 2.8, 7-2); 3.79 (1,q, J = 2.4, 7-CH); 6.62 (1, dd, J = 8.4, J = 2.0, -11);6.70 (1, d, J = 2.0, 4-CH); 6.86 (1, s, NH); 7.18 (1, d,J = 1.6, H-9); 7.62 (1, d, J = 8.4, H-12). 13C NMR spectrum,delta, ppm: 29.5; 30.9; 40.0; 47.5; 55.8; 57.0; 71.9; 113.0;113.6; 116.4; 122.2; 128.0; 136.4; 148.1; 148.2; 163.2; 188.1.Mass spectrum, m/z (Irel, %): 378 [M]+ (74), 363 [M-3]+(40), 299 [M-79Br]+ (39), 229 (13), 226 (13), 217 (40), 215(17), 193 (100), 152 (35), 148 (22), 147 (27), 119 (22).Found, %: 53.68; 4.41; Br 21.06; Cl 9.35; N 7.28.C17H16BrClN2O. Calculated, %: 53.78; 4.25; Br 21.04;Cl 9.34; N 7.38.
Statistics shows that 2-Amino-4-chlorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 38487-86-4.
Reference:
Article; Rozhkova, Yuliya S.; Vshivkova, Tatyana S.; Morozov, Vyacheslav V.; Zhulanov, Vladimir E.; Gorbunov, Aleksei A.; Shklyaev, Yurii V.; Chemistry of Heterocyclic Compounds; vol. 53; 11; (2017); p. 1228 – 1241; Khim. Geterotsikl. Soedin.; vol. 53; 11; (2017); p. 1228 – 1241,14;,
Nitrile – Wikipedia,
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