Water → 2-Cyclopropylmethyl-4-methyl-7-nitro-2h-isoquinolin-1-one

Participants

Reaction Steps

To 4-methyl-7-nitro-3,4-dihydro-2H-isoquinolin-1-one (0.90 g) in DMF (30 ml), sodium hydride (0.212 g, 60% suspension in oil) was added in portions. The mixture was stirred for 1 h then treated with cyclopropylmethyl bromide (0.72 g). The mixture was stirred for 4 h, poured into water and extracted with ethyl acetate. The organic phase was washed with water, dried (Na2SO4) and solvent removed at reduced pressure. The residue was column chromatographed (silica gel, DCM) to give the sub-title compound (0.22 g) as a yellow solid. 1H NMR δ: 0.43-0.54 (4H, m), 1.26 (1H, m), 2.30 (3H, s), 3.84 (2H, d, J 7.2 Hz), 7.70 (1H, s), 7.91 (1H, d, J=9.0 Hz), 8.50 (1H, dd, J=2.5, 8.9 Hz), 8.98 (1H, d, J=2.5 Hz).

Provenance & Evidence