Acetic Acid → 4-fluoro-3-(2-methyl-2-nitropropyl)-1H-indole

HRID 1272243

Reaction equation

HRID 1272243 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:11]N(C)C)=[CH:5][NH:6]2.[OH-].[Na+].C(O)(=O)C.[N+:21]([CH:24]([CH3:26])[CH3:25])([O-:23])=[O:22]>C(OCC)(=O)C.[Cl-].[Na+].O>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:11][C:24]([CH3:26])([N+:21]([O-:23])=[O:22])[CH3:25])=[CH:5][NH:6]2

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 3982-NitropropaneHCID 14798Sodium HydroxideHCID 27744704-Fluorogramine

Product 1

HCID 220148134-fluoro-3-(2-methyl-2-nitropropyl)-1H-indoleYield 76%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A slurry of 4-fluoro-3-(dimethylaminomethyl)-1H-indole (4.3 g, 22.4 mmol) in 14.1 ml of 2-nitropropane is treated with solid NaOH (941 mg, 23.5 mmol), and the resulting mixture is heated at reflux overnight. After cooling to ambient temperature, the reaction mixture is acidified with 10% aqueous acetic acid (25 ml) and stirring is continued for 30 minutes. The reaction mixture is diluted with ethyl acetate (50 ml) and brine (50 ml). The layers are separated, and the organic layer is washed with brine (50 ml), dried over Na2SO4 and concentrated in vacuo to give 3.71 g of 4-fluoro-3-(2-methyl-2-nitropropyl)-1H-indole (76%).

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureat reflux overnight
  3. customThe layers are separated
  4. washthe organic layer is washed with brine (50 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f4be0f806bef4bb58085178c54ef8bcb
Source dataset
uspto-grants-2007_04
Patent number
US07208505B2

Linked notes

Loading…