1H-Indole-2-carboxylic acid, 1-methyl- → 1-Methyl-1H-indole-3-carbonyl chloride

HRID 493487Notes

Reaction equation

HRID 493487 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:9]1C(O)=O>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

4

Reactant 2

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

Product 1

HCID 151324411-Methyl-1H-indole-3-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (7.1 mL, 81.4 mmol) in 50 mL of methylene chloride was added under nitrogen dropwise to a solution of 1-methyl-1H-indole carboxylic acid (2.86 g, 16.3 mmol) in 100 mL of methylene chloride at room temperature. After the addition the reaction was stirred at room temperature until the reaction was determined by NMR analysis to be complete. The solvent and excess oxalyl chloride were removed under reduced pressure. The residue was taken up in benzene and then concentrated to dryness under reduced pressure to give 1-methyl-1H-indole-3-carbonyl chloride, which was used in the following reaction without purification.

Workup

  1. additionAfter the addition the reaction
  2. customThe solvent and excess oxalyl chloride were removed under reduced pressure
  3. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-273b5be94cfd454e9cb7616130081e01
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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