Dimethylamine → 3-(dimethylamino)-N-(3-nitrophenyl)propanamide

Participants

Reaction Steps

To a stirred solution of 3-chloro-N-(3-nitrophenyl)propanamide (4.6 g, 20 mmol) in THF (50 mL) was added dropwise N,N-dimethyl amine (2M solution in THF) (1.8 g, 20 mL, 40 mmol) at room temperature. The resulting mixture was stirred at room temperature overnight and then evaporated to dryness under reduced pressure. The residue was triturated with 5% NH3 (aqueous, 50 mL) and the solid product was collected by filtration, washed with water followed by hexane, and dried to give 3-(dimethylamino)-N-(3-nitrophenyl)propanamide, 4.1 g (87%), mp 80-81° C. 1H NMR (DMSO-d6) δ: 2.17 (6H, s, CH3), 2.47-2.50 (2H, t, J=6.4 Hz, CH), 2.56-2.59 (2H, t, J=6.8 Hz, CH), 7.57-7.62 (1H, t, J=8.2 Hz, Ar—H), 7.88-7.91 (2H, dd, J=8.1 and 2.2 Hz, Ar—H), 8.63-8.64 (1H, t, J=2.0 Hz, Ar—H), 10.49 (1H, brs, NH).

Provenance & Evidence