Acetic Anhydride → 6-Acetamido-4-methyl-beta-carbolin-3-carboxylic acid ethyl ester

HRID 1757979Notes

Reaction equation

HRID 1757979 reaction equation
[CH2:1]([O:3][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])[CH3:2].[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1>[CH2:1]([O:3][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]([NH:20][C:21](=[O:23])[CH3:22])=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 130373386-Amino-4-methyl-beta-carboline-3-carboxylic-acid-ethylester

Product 1

HCID 130373396-Acetamido-4-methyl-beta-carbolin-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.6 g of 6-amino-4-methyl-β-carbolin-3-carboxylic acid ethyl ester is dissolved in 6 ml of pyridine and 1.5 ml of acetic anhydride and the whole is stirred for 16 hours at room temperature. The mixture is then stirred into 30 ml of ice water and intensely extracted with ethyl acetate. The extracts are washed until neutral with semisaturated common salt solution, dried using sodium sulphate and filtered. The solvent is distilled off in vacuo. The residue (0.78 g) is recrystallized from acetone-diisopropyl ether. 0.49 g of 6-acetamido-4-methyl-β-carbolin-3-carboxylic acid ethyl ester of melting point 273°-278° C. is obtained.

Workup

  1. extractionintensely extracted with ethyl acetate
  2. washThe extracts are washed until neutral with semisaturated common salt solution
  3. customdried
  4. filtrationfiltered
  5. distillationThe solvent is distilled off in vacuo
  6. customThe residue (0.78 g) is recrystallized from acetone-diisopropyl ether

Sources & evidence

ORD record
ord-c76bff1860a2467385fd35cd8a0555e5
Source dataset
uspto-grants-1983_02
Patent number
US04371536

Reaction notes

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