Dimethylformamide → 4-methyl-1H-indole-3-carbaldehyde

HRID 618102

Reaction equation

HRID 618102 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2.[OH-].[Na+].CN(C)[CH:20]=[O:21]>>[CH3:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[C:9]([CH:20]=[O:21])=[CH:10][NH:11]2

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 852824-Methylindole

Product 1

HCID 27624374-methyl-1H-indole-3-carbaldehyde

Procedure

A mixture of N,N-dimethylformamide (6 ml) and phosphorus oxychloride (1.78 g) was stirred at room temperature for 30 minutes. 4-Methylindole (1.0 g) was added to the reaction solution, followed by stirring at room temperature for one hour. A 5N aqueous solution of sodium hydroxide (15 ml) was added thereto, followed by stirring at 100° C. for further 30 minutes. The reaction solution was cooled, and the precipitated crystals were collected by filtration to give 4-methylindole-3-carboxaldehyde (Compound III-1, 1.14 g).

Workup

  1. stirringby stirring at room temperature for one hour
  2. stirringby stirring at 100° C. for further 30 minutes
  3. temperatureThe reaction solution was cooled
  4. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-1464b2d750214adcb2a09dab3d7b0285
Source dataset
uspto-grants-1999_09
Patent number
US05952355

Linked notes

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