Methyl chloroformate → HCID 16049828, compound

Participants

Reaction Steps

To a solution of 3-methyloxy-N′,2-diphenyl-4-quinolinecarbohydrazide (100 mg, 0.27 mmol) and Et3N (56 μL, 0.41 mmol) in CH2Cl2 (7 mL) was added methyl chloroformate (27 μL, 0.35 mmol). After stirring at room temperature for 4 h the mixture was diluted with CH2Cl2 and washed with 1N HCl (20 mL), 1N NaOH (20 mL) and brine (20 mL). The organic phase was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with isohexane:ethyl acetate (2:1), to afford the title compound (59 mg, 51%) as a colourless foam. 1H NMR (CDCl3, 360 MHz), δ 8.43 (1H, s), 8.16-8.13 (2H, m), 8.02-8.00 (2H, m), 7.69 (1H, dt, J=6.9 and 1.3 Hz), 7.61-7.41 (8H, m), 7.30 (1H, t, J=7.4 Hz), 3.91 (3H, s), 3.57 (3H, s). MS (ES+) C25H21N3O4 requires: 427, found: 428 (M+H+, 100%).

Provenance & Evidence