Methanol → methyl 1-methyl-1H-indole-7-carboxylate

HRID 564979ノート

反応式

HRID 564979 の反応式
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([OH:13])=[O:12])[CH:4]=[CH:3]1.S(Cl)(Cl)=O.[CH3:18]O>>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([O:13][CH3:18])=[O:12])[CH:4]=[CH:3]1

参加物

4

反応物 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 183883621-methyl-1H-indole-7-carboxylic acid

生成物 1

HCID 10821478methyl 1-methyl-1H-indole-7-carboxylate収率 59%

実験手順

To 70 ml of a methanol solution of 1.82 g (10.4 mmol) of 1-methyl-7-indolecarboxylic acid was added dropwise 3.09 g (26.0 mmol) of thionyl chloride at 0° C. The reaction mixture was refluxed for 2 hours and the solvent was then distilled off under reduced pressure. Ice water was poured onto the resulting residue and ammonium hydroxide was added to render the mixture alkaline. The mixture was extracted three times with ethyl acetate. The combined extracts were washed with water and dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue was isolated and purified by silica gel column chromatography to give 1.16 g (59.0%) of methyl 1-methyl-7-indolecarboxylate.

後処理

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. distillationthe solvent was then distilled off under reduced pressure
  3. additionIce water was poured onto the resulting residue and ammonium hydroxide
  4. additionwas added to render the mixture alkaline
  5. extractionThe mixture was extracted three times with ethyl acetate
  6. washThe combined extracts were washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was then distilled off under reduced pressure
  9. customThe residue was isolated
  10. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-fc9e6568bc884a6cab5f2fa22de64893
出典データセット
uspto-grants-2001_01
特許番号
US06169107A

反応ノート

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