Acetic Acid → Ethyl 4-acetamido-1-methyl-2-indolecarboxylate

HRID 1067806Notes

Reaction equation

HRID 1067806 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:6]2[CH3:11].[C:17](O)(=[O:19])[CH3:18]>N1C=CC=CC=1>[C:17]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:6]2[CH3:11])(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 13401554Ethyl 4-amino-1-methyl-1H-indole-2-carboxylate

Product 1

HCID 21194389Ethyl 4-acetamido-1-methyl-2-indolecarboxylateYield 97.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 20 ml of pyridine was dissolved 1.2 g (5.52 mmol) of ethyl 4-amino-1-methyl-2-indolecarboxylate. While stirring at room temperature, 10 ml of anhydrous acetic acid was added to the solution. After stirring for 2 hours at room temperature, the reaction mixture was poured onto ice water. The mixture was extracted three times with ethyl acetate. The combined extracts were washed with 1N hydrochloric acid and then with saturated sodium hydrogencarbonate solution. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel column chromatography to give 1.40 g (97.9%) of ethyl 4-acetamido-1-methyl-2-indolecarboxylate.

Workup

  1. stirringAfter stirring for 2 hours at room temperature
  2. additionthe reaction mixture was poured onto ice water
  3. extractionThe mixture was extracted three times with ethyl acetate
  4. washThe combined extracts were washed with 1N hydrochloric acid
  5. distillationThe solvent was then distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8fafba0dec45486cbf3514b715516c5b
Source dataset
uspto-grants-2001_06
Patent number
US06248772B1

Reaction notes

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