2-Methylindole → 62454-47-1

HRID 461393Notes

Reaction equation

HRID 461393 reaction equation
CC1NC2C(C=1)=CC=CC=2.C(Cl)(=O)C(Cl)=[O:13].[CH3:17][C:18]1[NH:19][C:20]2[C:25]([C:26]=1[C:27](=[O:31])[C:28](Cl)=[O:29])=[CH:24][CH:23]=[CH:22][CH:21]=2>C(OCC)C>[CH3:17][C:18]1[NH:19][C:20]2[C:25]([C:26]=1[C:27](=[O:31])[C:28]([OH:13])=[O:29])=[CH:24][CH:23]=[CH:22][CH:21]=2

Participants

5

Reactant 3

HCID 72242-MethylindoleHCID 65578Oxalyl chlorideHCID 123921962-Methyl-α-oxo-1H-indole-3-acetyl chloride

Product 1

HCID 1176958862454-47-1

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2-methylindole (32.8) in diethyl ether (300 ml.) was added at 30° to oxalyl chloride (35.0g.) diluted with diethyl ether (200 ml.). After stirring for 1 hour the precipitate of 2-methylindolylglyoxylyl chloride was collected by filtration and treated with methanol (300 ml.) to give the methyl ester of 2-methylindol-3-ylglyoxylic acid (30.0 g.) as a red powder m.p. 180°-183°.

Workup

  1. filtrationwas collected by filtration
  2. additiontreated with methanol (300 ml.)

Sources & evidence

ORD record
ord-828ad899fab9448fb28678ea726f6d6f
Source dataset
uspto-grants-1977_12
Patent number
US04062869

Reaction notes

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