Oxalyl chloride → 1H-indole-2-carbonyl Chloride

HRID 432480Notes

Reaction equation

HRID 432480 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.C(Cl)(=O)C([Cl:16])=O>ClCCl.CN(C)C=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([Cl:16])=[O:12]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 72899Indole-2-carboxylic acid

Product 1

HCID 118162081H-indole-2-carbonyl Chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of indole-2-carboxylic acid (0.742 g, 4.6 mmol) in dichloromethane (3 mL) was treated with oxalyl chloride (0.700 g, 5.52 mmol) and one drop of dimethyl formamide. 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 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-567179773e3d4f33a80496dd8144be39
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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