Ammonia → 5-Phenoxy-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

978 mg of 5(-4-aminophenoxy)-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester is suspended in 2 ml of water and 10 ml of a 50% tetrafluoroboric acid. After cooling to 0° C., it is mixed drop by drop with a solution of 224 mg of sodium nitrite in 2 ml of water and stirred at 0° C. for 1/2 hour. Then it is mixed at the same temperature with a 60% hypophosphoric acid and 150 mg of copper(I) oxide, diluted with 10 ml of water and afterwards heated for 1/2 hour on the steam bath. After adjustment of the pH to 8 with soda and addition of ammonia, it is extracted with ethyl acetate. The ethyl acetate phase is evaporated and the residue chromatographed over silica gel with acetone: hexane=1:1 as eluant. 540 mg (57% of theory) of 5-phenoxy-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester with a melting point of 174°-176° C. is obtained.

Provenance & Evidence