Dimethylamine → 6-amino-4-methyl-beta-carbolin-3-carboxylic acid N,N-dimethylamide
Reaction equation
C(O[C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH3:19])=[CH:15][C:14]([NH2:20])=[CH:13][CH:12]=3)=[O:5])C.[CH3:21][NH:22][CH3:23]>C(O)CO>[CH3:21][N:22]([CH3:23])[C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH3:19])=[CH:15][C:14]([NH2:20])=[CH:13][CH:12]=3)=[O:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
0.3 g of 6-amino-4-methyl-β-carbolin-3-carboxylic acid ethyl ester is suspended in 5 ml of ethylene glycol and, after the addition of 3 ml of dimethylamine, the whole is heated for 22 hours at 100° C. After cooling, the mixture is poured into 30 ml of ice water, extracted with ethyl acetate, washed with water until neutral, dried using sodium sulphate, filtered and the solvent is distilled off in vacuo. The crude product precipitates as a fine brown powder. 0.2 g of 6-amino-4-methyl-β-carbolin-3-carboxylic acid N,N-dimethylamide of melting point 235°-245° C. (decomposition) is obtained.
Workup
- temperatureAfter cooling
- extractionextracted with ethyl acetate
- washwashed with water until neutral,
- customdried
- filtrationfiltered
- distillationthe solvent is distilled off in vacuo
- customThe crude product precipitates as a fine brown powder
Sources & evidence
- ORD record
- ord-8df07157fe034aa080742835cc53c12d
- Source dataset
- uspto-grants-1983_02
- Patent number
- US04371536
Reaction notes
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