Glycerol → 8-Bromo-5,6,7-trimethylquinoline

Participants

Reaction Conditions

Reaction Steps

2-Bromo-3,4,5-trimethylaniline (10.4 g), glycerol (4 equiv) and arsenic oxide (0.75 equiv) were stirred and heated to 100° C. Concentrated sulfuric acid (60% w/w of the glycerol) was added to the mixture dropwise. After heating at 130° C. for 4 hr, the cooled mixture was diluted with water and neutralised with aqueous ammonia. The solid was filtered off, washed with water and dried in air. Purification by column chromatography over alumina with dichloromethane elution gave 8-bromo-5,6,7-trimethylquinoline as a white solid, mp 180° C. Pmr spectrum (CDCl3 ; δ in ppm): 2.50 (3H,s); 2.61 (3H,s); 2.74 (3H,s); 7.37-8.98 (3H,m).

Provenance & Evidence