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

HRID 1757984Notes

Reaction equation

N([O-])=O.[Na+].[CH2:5]([O:7][C:8]([C:10]1[N:11]=[CH:12][C:13]2[NH:14][C:15]3[C:20]([C:21]=2[C:22]=1[CH3:23])=[CH:19][C:18](N)=[CH:17][CH:16]=3)=[O:9])[CH3:6].[Cu][C:26]#[N:27]>S(=O)(=O)(O)O.[C-]#N.[Na+]>[CH2:5]([O:7][C:8]([C:10]1[N:11]=[CH:12][C:13]2[NH:14][C:15]3[C:20]([C:21]=2[C:22]=1[CH3:23])=[CH:19][C:18]([C:26]#[N:27])=[CH:17][CH:16]=3)=[O:9])[CH3:6]

Participants

Conditions

Temperature: 60 °C

Procedure

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 3 N 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.

Workup

waitto stand at room temperature for 2 hours
filtrationis then suction-filtered
extractionThe filter residue is extracted
concentrationThe combined filtrates are concentrated by evaporation
customchromatographed on silica gel with chloroform/ethanol (95:5)

Sources & evidence

ORD record: ord-d1ed95f0d72440dfbd174a4e338a8fbc
Source dataset: uspto-grants-1983_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04371536

Reaction notes

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