Dimethylformamide → 1-Methyl-1H-indole-3-carbonyl chloride

HRID 2355123Notes

Reaction equation

HRID 2355123 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH3:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)C(C(O)=O)=[CH:9]1.CN(C=O)C>C(Cl)Cl>[CH3:9][N:8]1[C:16]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:1]([C:2]([Cl:4])=[O:3])=[CH:7]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 8540401-Methylindole-3-carboxylic acid

Product 1

HCID 151324411-Methyl-1H-indole-3-carbonyl chlorideYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (5.0 mL, 57.3 mmol) was added under nitrogen to a solution of 1-methylindole-3-carboxylic acid (2.00 g, 11.4 mmol) in 150 mL of methylene chloride at room temperature. A catalytic amount of DMF (10 μL) was added and the reaction stirred at room temperature for 3 h. The solvent and excess oxalyl chloride were removed under reduced pressure. To remove any residual oxalyl chloride the residue was taken up in benzene and then concentrated under reduced pressure to give 1-methyl-1H-indole-3-carbonyl chloride (2.21 g, 99%) as a yellow solid that was used in the next step without additional purification

Workup

  1. customThe solvent and excess oxalyl chloride were removed under reduced pressure
  2. customTo remove any residual oxalyl chloride the residue
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-68df5879bb7a49afa5f0540a0ab2c464
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

Loading…