Methylamine → 4,5,7-Trichloro-2-methyl-1H-isoindole-1,3(2H)-dione

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,4,6-trichlorophthalic acid (25.01 g, 92.8 mmol) and glacial acetic acid (100 mL) was charged to a 250 mL 3-neck flask, equipped with a dry-ice condenser, thermometer, gas sparger and magnetic stirrer and maintained under an atmosphere of dry nitrogen. The mixture was heated and maintained at 50°-54° C. while methylamine (12 g, 0.4 mol) was introduced over a period of 1.5 hours. Following the addition of the methylamine, the reaction mixture was heated to 93° C. and maintained thereat for about 5 hours, then cooled to room temperature and filtered. The filter cake was washed with cold water and vacuum dried (0.2 mmHg) for 24 hours to yield 15.97 g of 3,4,6-trichloro-N-methylphthalimide as a white powder (m.p. 166°-167.5° C.).

Provenance & Evidence