1H-Indole-2-carboxylic acid, 1-methyl- → 1-Methyl-1H-indole-2-carbonyl chloride
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
Product 1
Reagents, catalysts & solvents 2
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 to purification or analysis.
Workup
- customThe solvent was removed under reduced pressure
- customdried on the high vacuum for 1 hour
- customThe residue was used directly in the subsequent reaction without
- customfurther to purification or analysis
Sources & evidence
- ORD record
- ord-e8861a176ae7430286f1dd410eb35148
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273736B2
Reaction notes
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