Dimethylformamide → 6-Ethyl-1H-indole-3-carbaldehyde

HRID 618130

Reaction equation

HRID 618130 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[CH:13][NH:14]2)=[CH:10][CH:9]=1)[CH3:7].[OH-].[Na+].CN(C)[CH:21]=[O:22]>>[CH2:6]([C:8]1[CH:16]=[C:15]2[C:11]([C:12]([CH:21]=[O:22])=[CH:13][NH:14]2)=[CH:10][CH:9]=1)[CH3:7]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 183302676-ethyl-1H-indole

Product 1

HCID 218501566-Ethyl-1H-indole-3-carbaldehyde

Procedure

Phosphorus oxychloride (3.82 g) was added to N,N-dimethylformamide (20 ml), and the mixture was stirred at room temperature for 10 minutes. A solution of 6-ethylindole [Journal of the Chemical Society (J. Chem. Soc.), 7165 (1965)] in N,N-dimethylformamide (6 ml) was added to the reaction solution, and the mixture was stirred at room temperature for one hour. Ice (20 g) and then a 5N aqueous solution of sodium hydroxide (34 ml) were added to the reaction solution, and the mixture was heated under reflux for one hour. The reaction solution was ice-cooled, and the precipitated crystals were collected by filtration to give 6-ethylindole-3-carboxaldehyde (2.76 g).

Workup

  1. stirringthe mixture was stirred at room temperature for one hour
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for one hour
  4. temperaturecooled
  5. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-20a4dc9d96584dd39f0523e402c8b79a
Source dataset
uspto-grants-1999_09
Patent number
US05952355

Linked notes

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