Ammonia → 1,2,3,4,-5,6-Hexahydro-6-methyl-8-hydroxy-11-oxo-2,6-methano-3-benzazocine

Participants

Reaction Steps

A mixture of 1,2,3,4,5,6-hexahydro-6-methyl-8-methoxy-11-oxo-2,6-methano-3-benzazocine (2.18 g.) and hydrobromic acid (48%, 20 ml.) was stirred under reflux (for 30 min.), basified with dilute ammonia and extracted with chloroform. Desiccation and concentration of the chloroform extracts afforded a tan solid (1.1 g.), recrystallization of which from acetone afforded 1,2,3,4,-5,6-hexahydro-6-methyl-8-hydroxy-11-oxo-2,6-methano-3-benzazocine (III: R=CH3, X"=HO, Y+Z=O; 0.4 g.), a white solid.

Provenance & Evidence