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

HRID 17153

Reaction equation

HRID 17153 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([OH:13])=O.C(Cl)(=O)C([Cl:17])=O>ClCCl.CN(C)C=O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([Cl:17])=[O:13]

Participants

5

Reactant 2

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

Product 1

HCID 123033141-Methyl-1H-indole-2-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 1-methyl-1H-2-indolecarboxylic acid (0.485 g, 2.769 mmol) in dichloromethane (10 mL) at 0° C. was treated with oxalyl chloride (0.369 g, 2.91 mmol) and one drop of dimethyl formamide. The reaction mixture was stirred at 0° C. for 1 hour and at room temperature for 2 hours. The solvent was removed under reduced pressure and dried on the high vacuum for 1 hour. The residue was used directly in the subsequent reaction without further purification or analysis.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customdried on the high vacuum for 1 hour
  3. customThe residue was used directly in the subsequent reaction without further purification or analysis

Sources & evidence

ORD record
ord-582438ec3357466097420a38f45a9681
Source dataset
uspto-grants-2010_06
Patent number
US07737160B2

Linked notes

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