Benzyl Chloride → 1-Benzyl-6-nitro-1H-indole

HRID 7060

반응식

HRID 7060 반응식
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[K+].C(OCC)(=O)C>CS(C)=O>[CH2:13]([N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=2)[CH:8]=[CH:9]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

6

반응물 4

HCID 7503Benzyl ChlorideHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 785026-Nitro-1H-indole

생성물 1

HCID 120793221-Benzyl-6-nitro-1H-indole수율 90%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

6-Nitroindole (1.0 g) and benzyl chloride (2.2 g) are dissolved in dimethylsulfoxide (10 ml), and thereto is added potassium hydroxide (1.0 g), and the mixture is stirred at room temperature for 12 hours. To the mixture is added ethyl acetate, and the organic layer is washed with water, dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give N-benzyl-6-nitroindole (1.4 g).

후처리

  1. washthe organic layer is washed with water
  2. dry with materialdried over sodium sulfate
  3. customthe solvent is evaporated under reduced pressure
  4. customThe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-97d243af42294beca3c2f10998f5b73c
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084176B2

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