6-Amino-4-methyl-beta-carboline-3-carboxylic-acid-ethylester → 6-Cyano-4-methyl-beta-carbolin-3-carboxylic acid ethyl ester

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Reaction Conditions

Reaction Steps

5 ml of 2 molar aqueous sodium nitrite solution is added dropwise, while cooling intensively with ice, to a suspension of 2.7 g of 6-amino-4-methyl-β-carbolin-3-carboxylic acid ethyl ester in 15 ml of 3N sulphuric acid. After 20 minutes, the diazotizing solution is quickly added dropwise to a solution at 60° C. of 1.2 g of copper (I) cyanide in 8 ml of 4.5 molar sodium cyanide solution. After heating for 30 minutes at 60° C., the solution is allowed to stand at room temperature for 2 hours and is then suction-filtered. The filter residue is extracted by boiling with methanol. The combined filtrates are concentrated by evaporation and chromatographed on silica gel with chloroform/ethanol (95:5). 6-Cyano-4-methyl-β-carbolin-3-carboxylic acid ethyl ester of melting point 268°-276° C. (decomposition) is obtained in 25% yield.

Provenance & Evidence