Dimethylformamide → 1H-Indole-2-carboxamide
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.C(Cl)(=O)C(Cl)=O.C[N:20](C=O)C>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH2:20])=[O:12]Participants
4
Procedure
To a solution of indole-2-carboxylic acid (1 g, 6.21 mmol) in MC (30 ml), oxalyl chloride (1.64 ml, 0.18.62 mmol) and a catalytic amount of DMF were added and stirred at room temperature for 2 hrs. After the solvent was evaporated, the crude acyl chloride was diluted with MC (20 ml), to which a solution of ammonium hydroxide in water (7 ml) was dropwise added with cooling in an ice bath. After stirring for 1 hr, the precipitated product was collected by suction filtration, triturated in hexane and dried to give the title compound, which was used in the next step without further purification.
Workup
- customAfter the solvent was evaporated
- additionthe crude acyl chloride was diluted with MC (20 ml), to which a solution of ammonium hydroxide in water (7 ml)
- additionwas dropwise added
- temperaturewith cooling in an ice bath
- stirringAfter stirring for 1 hr
- filtrationthe precipitated product was collected by suction filtration
- customtriturated in hexane
- customdried
Sources & evidence
- ORD record
- ord-57c2c8ae81e348d69f89dbe868afc544
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07662960B2
Reaction notes
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