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

HRID 897765Notes

Reaction equation

HRID 897765 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-965cac7eb6a94d8da1a0f4c58eb007ed
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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