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

HRID 1072615

반응식

HRID 1072615 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-c436e43a9bc649c5a858135425629572
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06911463B2

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