Diazomethane → methyl 1H-indole-5-carboxylate

HRID 2270968Notes

Reaction equation

HRID 2270968 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[N+](=[CH2:15])=[N-]>CCOCC>[CH3:15][O:11][C:10]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][CH:2]=[CH:3]2)=[O:12]

Participants

4

Reactant 2

HCID 9550Diazomethane2×HCID 742801H-Indole-5-Carboxylic Acid

Product 1

HCID 2737635methyl 1H-indole-5-carboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4.8 g (29.8 mmol) of indole-5-carboxylic acid in ether (200 ml) was added dropwise etheral diazomethane until the yellow color of diazomethane did not disappear. The mixture was concentrated and the obtained residue was chromatographed on silica gel (ethyl acetate as an eluant) to give 4.5 g of indole-5-carboxylic acid methyl ester. Yield: 86%.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe obtained residue was chromatographed on silica gel (ethyl acetate as an eluant)

Sources & evidence

ORD record
ord-fd619b0a480440fb82e6d6b0d16a34dd
Source dataset
uspto-grants-2001_12
Patent number
US06333323B1

Reaction notes

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