3-Nitroaniline → 3-chloro-N-(3-nitrophenyl)propanamide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-nitroaniline (37a, 6.9 g, 50 mmol) in THF (50 mL) was added dropwise 3-chloropropionyl chloride (10 mL, 100 mmol) over 30 min under argon atmosphere. The reaction was stirred at 50° C. for 10 h. After cooling, the reaction mixture was evaporated to dryness under vacuo and the residue was neutralized with saturated aqueous solution of NaHCO3 and the solid product was collected by filtration, washed with water followed by hexane, and dried to afford 3-chloro-N-(3-nitrophenyl)propanamide, 10.61 g (92%), mp 86-88° C. (Lit. 100-102° C.57). 1H NMR (DMSO-d6) δ: 2.87-2.90 (2H, t, J=9.9 Hz, CH2), 3.90-3.92 (2H, t, J=9.9 Hz, CH2), 7.61-7.64 (1H, t, J=6.6 and 6.6 Hz, Ar—H), 7.90-7.94 (2H, m, Ar—H), 8.65-8.66 (1H, t, J=3.4 and 1.7 Hz, Ar—H), 10.59 (1H, brs, NH).

Provenance & Evidence