Indole → 3-m-Nitrobenzoylindole

HRID 249134Notes

Reaction equation

HRID 249134 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].[Cl-].[Al+3].[Cl-].[Cl-].[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18]1.C(OCC)(=O)C>ClCCl>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([C:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[NH:17][CH:18]=1)=[O:8])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 798IndoleHCID 8495Benzoyl chloride, 3-nitro-HCID 8857Ethyl AcetateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 98382063-m-NitrobenzoylindoleYield 34.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 3-nitrobenzoyl chloride (4.76 g) in dichloromethane (20 ml) was added to a suspension of aluminum chloride (3.42 g) in dichloromethane (50 ml) at 25° C., and the mixture was stirred at the same temperature for an hour. A solution of indole (3.0 g) in dichloromethane (20 ml) was added to the mixture at 25° C. After stirring for an hour at 25° C., the reaction mixture was poured into a mixture of ethyl acetate and ice water. The organic layer was separated, washed with water, and dried over magnesium sulfate. After evaporation of solvent, the crystalline residue was recrystallized from ethyl acetate to give 3-(3-nitrobenzoyl)indole (2.37 g) as pale red crystals. The mother liquid was purified by column chromatography on silica gel (20 g) with chloroform as eluent to give another crystals of 3-(3-nitrobenzoyl)indole (0.277 g).

Workup

  1. stirringAfter stirring for an hour at 25° C.
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of solvent
  6. customthe crystalline residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-948135161ad247c08442bfa41733fbe7
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Reaction notes

Loading…