Dichloromethane → 1-benzylindole-3-carbonyl Chloride

HRID 1357260Notes

Reaction equation

HRID 1357260 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([OH:19])=O)=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:23])=O.C(Cl)Cl>CN(C=O)C>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([Cl:23])=[O:19])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 336711-benzyl-1H-indole-3-carboxylic acidHCID 65578Oxalyl chloride

Product 1

HCID 104922281-benzylindole-3-carbonyl ChlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-benzyl-1H-indole-3-carboxylic acid (3.36 g, 13.37 mmol), oxalyl chloride (5.83 mL, 66.85 mmol), 100 mL methylene chloride and a catalytic amount of DMF was stirred at room temperature under nitrogen for 18 h (overnight). The solvent was removed under reduced pressure. To remove excess oxalyl chloride benzene was added and the solvent removed under reduced pressure to give 1-benzyl-1H-indole-3-carbonyl chloride as a brown oil (13.37 mmol) which was immediately used in step 2 without additional purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customTo remove excess oxalyl chloride benzene
  3. additionwas added
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-0bf60df8a1c74795bc21d394634198d6
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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