Bromide ion → Benzenamine, hydrobromide (1:1)

Participants

Reaction Steps

Frankel et al [Israel J. Chem. 1, 379-84 (1963)] found that carbonyl attack on, and resulting ring opening of, alpha-bromo-gamma-butyrolactone by aniline is favored over bromide displacement (alkylation) at high temperature (100° C. vs. 0° ). In Frankel, an excess of aniline was contacted with alpha-bromo-gamma-butyrolactone to give alpha-phenylamino-gamma-butyrolactone after aniline hydrobromide salt was removed. The alpha-phenylamino-gamma-butyrolactone was stirred with a 10% aqueous solution of sodium hydroxide resulting in hydrolysis or fission of the lactone ring to yield alpha-phenylamino-gamma-hydroxy butyranilide.

Provenance & Evidence