1H-Indole-2-carboxylic acid, 1-methyl- → 1-Methyl-1H-indole-2-carbonyl chloride

HRID 432450Notes

Reaction equation

HRID 432450 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([OH:13])=O.C(Cl)(=O)C([Cl:17])=O>ClCCl.CN(C)C=O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([Cl:17])=[O:13]

Participants

5

Reactant 2

HCID 276951H-Indole-2-carboxylic acid, 1-methyl-HCID 65578Oxalyl chloride

Product 1

HCID 123033141-Methyl-1H-indole-2-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of 1-methylindole-2-carboxylic acid (0.805 g, 4.6 mmol) in dichloromethane (3 mL) was treated with oxalyl chloride (0.700 g, 5.52 mmol) and one drop of dimethylformamide. The reaction mixture was shaken for 18 h. The solvent was removed under reduced pressure and dried under high vacuum to afford a quantitative amount of 1-methyl-1H-2-indolecarbonyl chloride. The oil was directly used in the following reaction.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-d403d86ffd2d42d7b1ef09dc00d6aca5
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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