Dimethylformamide → N-cyclopentylmethyl-3-formylindole-6-acetamide

HRID 330144Notes

Reaction equation

HRID 330144 reaction equation
P(Cl)(Cl)(Cl)=O.[CH:6]1([CH2:11][NH:12][C:13](=[O:24])[CH2:14][C:15]2[CH:23]=[C:22]3[C:18]([CH:19]=[CH:20][NH:21]3)=[CH:17][CH:16]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+].CN(C)[CH:29]=[O:30]>>[CH:6]1([CH2:11][NH:12][C:13](=[O:24])[CH2:14][C:15]2[CH:23]=[C:22]3[C:18]([C:19]([CH:29]=[O:30])=[CH:20][NH:21]3)=[CH:17][CH:16]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 14882504N-cyclopentylmethylindole-6-acetamide

Product 1

HCID 53983395N-cyclopentylmethyl-3-formylindole-6-acetamideYield 58%

Procedure

N,N-dimethylformamide (0.53 ml) was cooled to 0° under an atmosphere of nitrogen and treated with phosphorus oxychloride (0.17 ml). This solution was stirred at 0° for 15 min and treated with a solution of N-cyclopentylmethylindole-6-acetamide (Example 1, part h), (0.40 g) in N,N-dimethylformamide (4 ml). The yellow mixture was stirred for 30 min 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 min and allowed to cool. The precipitate which formed was collected by filtration to give N-cyclopentylmethyl-3-formylindole-6-acetamide (0.26 g, 58%) as a tan powder; partial NMR (80 MHz, DMSO-d6): 2.96(t, 2H, NHCH2), 3.48(s, 2H, COCH2), 7.21(dd, 1H, H5 -indole), 7.38(br s, 1H, H2 -indole), 9.88(s, 1H, CHO).

Workup

  1. stirringThe yellow mixture was stirred for 30 min
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 5 min
  4. temperatureto cool
  5. customThe precipitate which formed
  6. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-e5eee0ff01fe48c3ba43d47e6cc460a9
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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