Methylamine → 5-Bromo-2-methyl-2,3-dihydro-1H-isoindol-1-one

Participants

Reaction Conditions

Reaction Steps

Methyl 4-bromo-2-(bromomethyl)benzoate (0.153 g, 0.497 mmol) was suspended in methanamine (2M solution in MeOH, 2.484 mL, 4.97 mmol) and the mixture was heated to reflux (90° C.) for 24 hours. The reaction mixture was cooled, concentrated in vacuo, and dried under high vacuum to give the title compound (0.112 g). 1H NMR (500 MHz, CDCl3) δ ppm 3.19 (s, 3 H), 4.36 (s, 2 H), 7.57-7.62 (m, 2 H), 7.70 (d, J=8.30 Hz, 1 H); ESI-MS m/z [M+H]+ 226.3.

Provenance & Evidence