Phenyl chloroformate → Phenyl methyl(2-(6-nitro-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamate

Participants

Reaction Steps

A solution of N,N-dimethyl-2-(6-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanamine (500 mg, 2.01 mmol) in 10 mL CH2Cl2 was treated dropwise with phenylchloroformate (378 μL, 3.01 mmol). The reaction was stirred at room temperature for 17 hours then partitioned between CH2Cl2 100 mL and 1N NaOH (20 mL). After extraction, the organic layer was separated, dried over Na2SO4, filtered and concentrated to give a yellow residue. This residue was subjected to flash chromatography on silica gel using 20% EtOAc/CH2Cl2 to give a yellow residue (610 mg, 85.4%). 1H-NMR (CDCl3) δ 7.99-7.92 (m, 1H), 7.87 (d, J=2.1 Hz, 1H), 7.39-7.33 (m, 2H), 7.23-7.19 (m, 1H), 7.06-7.01 (m, 2H), 6.69 (m, 1H), 3.67-3.52 (m, 4H), 3.48 (t, J=5.7 Hz, 2H), 3.14 and 3.07 (2×s, 3H), 2.79 (t, J=6.3 Hz, 2H), 1.99-1.96 (m, 2H). MS (ESI): 356.2 (M+1).

Provenance & Evidence