Methyl iodide → 4-Chloro-1-methyl-1H-indole

HRID 1155684

반응식

HRID 1155684 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[OH-].[Na+].[CH3:13]I>C1C=CC=CC=1>[CH3:13][N:6]1[C:7]2[C:3](=[C:2]([Cl:1])[CH:10]=[CH:9][CH:8]=2)[CH:4]=[CH:5]1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 913454-Chloroindole

생성물 1

HCID 130487594-Chloro-1-methyl-1H-indole

시약·촉매·용매 1

HCID 241Benzene용매

반응 조건

온도
40 °C

실험 절차

A mixture of 60 g of 4-chloro-1H-indole, 400 ml of benzene, 200 ml of 50% sodium hydroxide solution, 68 g of n-tetrabutylammonium hydrogen sulfate and 68 ml of methyl iodide was stirred at 40° C. for 4 hours and was then cooled. The decanted aqueous phase was extracted with ethyl acetate and the combined organic phases were washed with aqueous sodium chloride, dried over magnesium sulfate and distilled to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with an 8-2 cyclohexanebenzene mixture to obtain 63.85 g of 1-methyl-4-chloro-1H-indole.

후처리

  1. temperaturewas then cooled
  2. extractionThe decanted aqueous phase was extracted with ethyl acetate
  3. washthe combined organic phases were washed with aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. distillationdistilled to dryness under reduced pressure
  6. customThe residue was chromatographed over silica gel
  7. washwas eluted with an 8-2 cyclohexanebenzene mixture

출처 및 근거

ORD 기록
ord-c455ac1d250d4d4b9ed770be0bfa4e25
출처 데이터셋
uspto-grants-1982_06
특허 번호
US04332808

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