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

HRID 1357274Notes

Reaction equation

HRID 1357274 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>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 65578Oxalyl chlorideHCID 8540401-Methylindole-3-carboxylic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (11.86 mL, 136 mmol) was added dropwise to a solution of 1-methyl-1H-indole-3-carboxylic acid (4.76 g, 27 mmol) in 100 mL of methylene chloride. A rapid evolution of gas was observed. The reaction stirred at room temperature for 17 h (overnight). The solvent was removed under reduced pressure to give a pink solid To remove any excess oxalyl chloride the solid was dissolved in benzene and the solvent removed under reduced pressure to give 1-methyl-1H-indole-3-carbonyl chloride which was immediately used in step 2 without additional purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto give a pink solid
  3. customTo remove any excess oxalyl chloride the solid
  4. dissolutionwas dissolved in benzene
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-ac1c380e6a4247fd88f715544d9dfbdd
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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