Cyclopropylamine → 2-(cyclopropylamino)-N-methyl-3-nitrobenzamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-N-methyl-3-nitrobenzamide (830 mg, 3.20 mmol), cyclopropanamine (666 μL, 9.61 mmol) in THF (10 mL) under N2 was heated at 60° C. for 18 h. The reaction mixture was diluted with EtOAc, washed with water and brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatography on a silica gel column using DCM-EtOAc (1:1) as eluent to give 2-(cyclopropylamino)-N-methyl-3-nitrobenzamide: 1H NMR (400 MHz, DMSO-d6) δ 8.54-8.47 (m, 2H), 7.95 (dd, J=8, 4 Hz, 1H), 7.64 (dd, J=8, 4 Hz, 1H), 6.77 (dd, J=8, 4 Hz, 1H), 2.76 (d, J=8 Hz, 3H), 2.68-2.62 (m, 1H), 0.67-0.60 (m, 2H), 0.44-0.40 (m, 2H); LC-MS (ESI) m/z 236.1 [M+H]+.

Provenance & Evidence