Dimethylformamide → 1-Methyl-1H-indole-2-carbonyl chloride

HRID 898059Notes

Reaction equation

HRID 898059 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.CN(C=O)C>ClCCl>[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 3

HCID 6228DimethylformamideHCID 276951H-Indole-2-carboxylic acid, 1-methyl-HCID 65578Oxalyl chloride

Product 1

HCID 123033141-Methyl-1H-indole-2-carbonyl chlorideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 1-methylindole-2-carboxylic acid (9.87 g, 56.4 mmol) in dichloro-methane (150 mL) was reacted with oxalyl chloride (8.58 g, 67.63 mmol). DMF was added (0.2 mL), upon which a vigorous reaction transpired. The mixture was stirred at ambient temperature for four hours. The solvent was removed in vacuo to give 1-methyl-1H-2-indolecarbonyl chloride (10.69 g, 98%) as a light yellow solid.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-decc16c1475f4e66981f0c2c4333985b
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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