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

HRID 1155684

反応式

HRID 1155684 の反応式
[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

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 913454-Chloroindole

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

反応条件

温度
40 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c455ac1d250d4d4b9ed770be0bfa4e25
出典データセット
uspto-grants-1982_06
特許番号
US04332808

関連ノート

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