Methanol → 8-amino-2-methyl-3,4-dihydroisoquinolin-1(2H)-one

Participants

Reaction Steps

A solution of 8-amino-2-methylisoquinolin-1(2H)-one (Compound 131A, 100 mg, 0.54 mmol) in acetic acid (10 mL) was hydrogenated over PtO2 (24 mg) at room temperature for 16 h. TLC (5% MeOH in CH2Cl2) showed the reaction was complete. The catalyst was filtered off through Celite and the filtrate was evaporated to dryness to give a residue, which was dissolved in EtOAc (20 mL), washed with aq. sat. NaHCO3 (20 mL), water (10 mL), dried and evaporated, residue was purified by column chromatography on silica gel (5% MeOH in CH2Cl2) to give the desired product (25 mg, 25%). 1H NMR (CDCl3, 300 MHz): δ=2.96 (t, J=6.6 Hz, 2 H), 2.98 (s, 3 H), 3.55 (t, J=6.9 Hz, 2 H), 6.18 (br, 2 H), 6.45 (d, J=6.9 Hz, 1 H), 6.58 (d, J=7.5 Hz, 1 H), 7.15 (t, J=7.5 Hz, 1 H).

Provenance & Evidence