Diphenyl Ether → 7-Chloro-3-methyl-1(2H)-isoquinolinone

Participants

Reaction Conditions

Reaction Steps

3-(4-Chlorophenyl)-2-methyl-acryloyl azide (11.0 g, 50 mmol) is dissolved in 80 mL of diphenyl ether. The solution is added dropwise to a solution of tributyl amine (11.8 mL, 50 mmol) in 170 mL of diphenyl ether at 210° C. After 4 hours., the solution is cooled 50° C. and diluted with 1.5 L of hexanes. The resulting solid is collected by filtration giving the title compound as a white solid (7.2 g, 37 mmol). 1H NMR (d6-DMSO, 300 MHz) δ11.4 (bs, 1H), 8.02 (s, 1H), 7.67 (d, 1H), 7.55 (d, 1H), 6.34 (s, 1H), 2.18 (s, 3H).

Provenance & Evidence