Dimethylformamide → 1H-Indole-6-carboxamide, N-(cyclopentylmethyl)-3-formyl-

HRID 1198957Notes

Reaction equation

HRID 1198957 reaction equation
P(Cl)(Cl)(Cl)=O.[CH:6]1([CH2:11][NH:12][C:13]([C:15]2[CH:23]=[C:22]3[C:18]([CH:19]=[CH:20][NH:21]3)=[CH:17][CH:16]=2)=[O:14])[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+].CN(C)[CH:28]=[O:29]>>[CH:6]1([CH2:11][NH:12][C:13]([C:15]2[CH:23]=[C:22]3[C:18]([C:19]([CH:28]=[O:29])=[CH:20][NH:21]3)=[CH:17][CH:16]=2)=[O:14])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 149485056-(N-cyclopentylmethylcarbamoyl)indole

Product 1

HCID 99932821H-Indole-6-carboxamide, N-(cyclopentylmethyl)-3-formyl-Yield 60%

Procedure

N,N-Dimethylformamide (DMF)(20 ml) was cooled to 0° under an atmosphere of nitrogen and treated cautiously with phosphorus oxychloride (6.6 ml). This solution was stirred at 0° for 15 minutes, warmed to room temperature, and treated with a solution of 6-(N-cyclopentylmethylcarbamoyl)indole (14.3 g) in DMF (100 ml). The yellow mixture was stirred for 2 hours and then brought to pH 14 by the addition of ice and 20% (w/v) aqueous sodium hydroxide. The mixture was heated to reflux for 5 minutes and allowed to cool. The precipitate which formed was collected by filtration and triturated with ether to give 6-(N-cyclopentylmethylcarbamoyl)-3-formylindole (9.6 g, 60%) as a tan powder; mp 224°-225°.

Workup

  1. stirringThe yellow mixture was stirred for 2 hours
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 5 minutes
  4. temperatureto cool
  5. customThe precipitate which formed
  6. filtrationwas collected by filtration
  7. customtriturated with ether

Sources & evidence

ORD record
ord-d39396d44e4f48718bc77a760dc6daaa
Source dataset
uspto-grants-1990_02
Patent number
US04898863

Reaction notes

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