HCID 67271496, compound → HCID 67271462, compound

Participants

Reaction Steps

To a suspension of 1,2-dihydro-6-nitroisoquinolin-3(4H)-one (10.3 g, 53.6 mmol) in MeOH (150 mL) was added 10% Pd/C (1.14 g, 1.07 mmol) and the mixture was stirred overnight under H2 (1 atm). After filtration, the filtrate was concentrated and the residue was suspended in acetone, filtered and precipitated with conc. HCl (10 mL). The resulting precipitate was collected, washed with H2O and acetone and recrystallized from MeOH/H2O to yield 6-amino-1,2-dihydroisoquinolin-3(4H)-one as a grey solid (6.7 g, 63% yield). 1H NMR (400 MHz, CD3OD): δ 7.22 (d, J=2.0 Hz, 1H), 7.20 (dd, J=8.4, and 2.4 Hz, 1H), 6.98 (d, J=8.4 Hz, 1H), 3.01 (t, J=7.6 Hz, 2H), 2.59 (t, J=7.6 Hz, 2H); MS (ESI) m/z: 163.0 (M+H+).

Provenance & Evidence