Sodium Hydroxide → HCID 55283162, compound

Participants

Reaction Conditions

Reaction Steps

Amide 11 (3.0 g, 9.1 mmol) was dissolved in 50 ml of distillated ethanol and 50 ml of 3 M aqueous solution of NaOH was added. All was stirred at 20° C. for 24 h and evaporated to aqueous residue and 32 ml of 5 M HCl was added. It was extracted twice with 40 ml of dichloromethane. The aqueous layer was alkalified with sodium carbonate to pH=8 and extracted three times with 50 ml of diethyl-ether. Organic layers were combined and dried over anhydrous sodium sulphate. Filtration and evaporation yields 1.20 g (72%) of yellow oil; 1H NMR (CDCl3) δ: 1.72 (2H, bs, NH2), 5.18-5.24 (1H, m, CH2), 5.30-5.38 (1H+1H, m, CHCH2+ArCHNH2), 6.15-6.27 (1H, m, CHCH2), 7.42-7.60 (4H, m, ArH), 7.74-7.78 (m, 1H, ArH), 7.84-7.89 (m, 1H, ArH), 8.20 (d, 1H, J=8.3 Hz, ArH) ppm; 13C NMR (CDCl3) δ: 53.92 (CNH2), 114.28 (CH2), 123.41 (CH), 123.51 (CH), 125.55 (CH), 125.56 (CH), 126.05 (CH), 127.80 (CH), 128.92 (CH), 131.40 (C), 134.00 (C), 141.71 (CH) ppm.

Provenance & Evidence