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

HRID 1067767노트

반응식

HRID 1067767 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

HCID 10821478methyl 1-methyl-1H-indole-7-carboxylate수율 59%

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4e5ff870f7ce45139de9dd7237a199c7
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248772B1

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