Dimethylamine → 5-(Dimethylamino)isoindolin-1-one

Participants

Reaction Conditions

Reaction Steps

A 500-mL high-pressure bomb reactor was charged with 123b (2.20 g, 14.5 mmol) ethanol (30 mL) and excess dimethylamine (50 mL). The mixture was heated at 165° C. for 36h. After this time, the mixture was concentrated and the resulting residue was purified by flash column chromatography (silica, 98:2 ethyl acetate/triethyl-amine) to afford an 81% yield (2.40 g) of 123c as a yellow solid: mp 122-124° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.99 (s, 1H), 7.44 (d, 1H, J=9.3 Hz), 6.77 (m, 2H), 4.24 (s, 2H), 2.99 (s, 6H).

Provenance & Evidence