Phenylacetyl chloride → 1-(5-Nitro-indol-1-yl)-2-phenyl-ethanone

HRID 1517938Notes

Reaction equation

HRID 1517938 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[H-].[Na+].[C:15]1([CH2:21][C:22](Cl)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:22](=[O:23])[CH2:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:8]=[CH:7]2)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 7679Phenylacetyl chlorideHCID 225235-NitroindoleHCID 24758Sodium hydrideHCID 25517Ammonium Chloride

Product 1

HCID 593348921-(5-Nitro-indol-1-yl)-2-phenyl-ethanone

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

300 mg 5-nitroindole are dissolved in 10 ml of tetrahydrofuran. 81 mg sodium hydride (60% in mineral oil) are added and the mixture is stirred for 1 hour at ambient temperature. Then 294 μl phenylacetic acid chloride are added dropwise and the mixture is stirred for another 3 hours. It is divided between saturated ammonium chloride solution and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined organic phases are dried on magnesium sulphate. The solvents are eliminated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 10:1 to 1:3).

Workup

  1. stirringthe mixture is stirred for another 3 hours
  2. extractionThe aqueous phase is extracted with ethyl acetate
  3. customthe combined organic phases are dried on magnesium sulphate
  4. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 10:1 to 1:3)

Sources & evidence

ORD record
ord-b65deb02a7914a9597000053f2ca916a
Source dataset
uspto-grants-2012_07
Patent number
US08232312B2

Reaction notes

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