Urea → 5-Amino-2-methyl-6-nitroisoindoline-1,3-dione

Participants

Reaction Conditions

Reaction Steps

5-Chloro-2-methyl-6-nitroisoindoline-1,3-dione (14.40 g, 59.85 mmol) and urea (35.95 g, 599 mmol) were mixed together under argon. The mixture was stirred and heated to 150° C. for 3 h and cooled to rt. The solid was washed with 200 mL of hot water (90° C.) and filtered to remove the remaining urea. The isolated yellow solid was washed twice with hot water, dried under vacuum and purified by column chromatography (silica-gel CH2Cl2/acetone=19/1 v/v) to give a yellow solid product, 8.75 g, 66.1% yield. MS: 219.6 [M−H]−. 1H NMR (DMSO-d6, 500 MHz): δ 8.39 (s, 2H), 8.26 (s, 1H), 7.40 (s, 1H), 2.99 (s, 3H).

Provenance & Evidence