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

HRID 897742Notes

Reaction equation

HRID 897742 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-218232e7678246ad89360bd77863fa26
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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