1-benzyl-1H-indole-3-carboxylic acid → 1-benzylindole-3-carbonyl Chloride

HRID 493492

Reaction equation

HRID 493492 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH2:7]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)C(C(O)=O)=[CH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(Cl)Cl>[CH2:7]([N:14]1[C:22]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:1]([C:2]([Cl:4])=[O:3])=[CH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 336711-benzyl-1H-indole-3-carboxylic acidHCID 65578Oxalyl chloride3×

Product 1

HCID 104922281-benzylindole-3-carbonyl Chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (7.1 mL, 81.4 mmol) was added under nitrogen dropwise over 10 minutes to a suspension of 1-benzyl-1H-indole-3-carboxylic acid (4.10 g, 16.3 mmol) in 200 mL of methylene chloride at room temperature. When the oxalyl chloride was added there was an immediate evolution of gas and within 30 minutes all of the solid had dissolved. After the addition of the oxalyl chloride the reaction was stirred at room temperature for 2 h. 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-benzyl-1H-indole-3-carbonyl chloride, which was used in the following reaction without purification.

Workup

  1. dissolutionwithin 30 minutes all of the solid had dissolved
  2. customThe solvent and excess oxalyl chloride were removed under reduced pressure
  3. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-077fa6822c9143789210fa82aad8b7a5
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Linked notes

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