Ammonia → HCID 17972763, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-benzyl-11-hydroxy-7,8,9,10-tetrahydro-5H-benzo[b]carbazol-1-carboxylic acid, methyl ester, (0.097 g, 0.25 mM) in 8 mL THF was placed in an Ace Glass pressure tube (203 mm×38 mm) with a small stirring bar. A N2(g) stream was installed over the solution surface. The pressure tube and reaction solution were cooled to −78° C., and ˜8 mL NH3(l) was condensed into the reaction vessel by introduction of an NH3(g) stream. The pressure tube was sealed with a teflon O-ring screw cap, the resultant brown solution stirred at −78° C. for 10 minutes, then the cooling bath was removed and the reaction solution allowed to warm to ambient temperature behind a blast shield. After 24 h, the pressure tube was re-cooled to −78° C. and the internal NH3(g) pressure was released by careful removal of the Teflon cap. The reaction solution was allowed to slowly warm to room temperature while NH3(g) bubbled off, then the solution was concentrated in vacuo to afford 0.92 g (quantitative) of the title compound 5-benzyl-11-hydroxy-7,8,9,10-tetrahydro-5H-benzo[b]carbazole-1-carboxylic acid amide as a tan solid (MP 225° C. dec, MW 370.46).

Provenance & Evidence