Dimethylformamide → 1H-indole-2-carbonyl Chloride

HRID 1984297Notes

Reaction equation

HRID 1984297 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.CN(C)C=O>C(Cl)Cl>[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 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 72899Indole-2-carboxylic acid

Product 1

HCID 118162081H-indole-2-carbonyl ChlorideYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of indole-2-carboxylic acid (800 mg, 4.9 mmol) in CH2Cl2 was added oxalyl chloride (1.28 mL, 14.9 mmol) and N,N-dimethylformamide (DMF; 0.05 mL). After 1.5 h at 40° C., the mixture was concentrated to give a yellow solid (874 mg, 98%), which was used without purification in subsequent reactions.

Workup

  1. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-189fb7c7accf45d1bd7b2819748ca57a
Source dataset
uspto-grants-2009_06
Patent number
US07544698B2

Reaction notes

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