Ethyl 2-azido-3-(2-methoxyphenyl)propenoate → Ethyl 4-methoxy-1H-indole-2-carboxylate

HRID 2185677Notes

Reaction equation

HRID 2185677 reaction equation
[N:1]([C:4](=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+]=[N-]>C1(C)C=CC=CC=1>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[CH:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[NH:1]2

Participants

3

Reactant 1

HCID 72978722Ethyl 2-azido-3-(2-methoxyphenyl)propenoate

Product 1

HCID 11458647Ethyl 4-methoxy-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 2-azido-3-(2-methoxyphenyl)propenoate (3.566 g, 144 mmol) was suspended in toluene (800 ml) and the mixture was refluxed for three hours, then cooled and stirred at room temperature overnight. The ethyl 4-methoxyindole-2-carboxylate formed as a yellow solid and was collected.

Workup

  1. temperaturethe mixture was refluxed for three hours
  2. temperaturecooled

Sources & evidence

ORD record
ord-b57d6b7a1a364679b5182a384798cc31
Source dataset
uspto-grants-2002_06
Patent number
US06403561B1

Reaction notes

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