Hydrochloric Acid → Methyl 2,3-dihydro-1H-indole-7-carboxylate

HRID 568792노트

반응식

HRID 568792 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][CH:11]=[CH:10]2)=[O:4].[B-][N+](C)(C)C.Cl.[OH-].[Na+]>O1CCOCC1.CCOCC.O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][CH2:11][CH2:10]2)=[O:4]

참가 물질

8

반응물 4

HCID 313Hydrochloric Acid2회HCID 14798Sodium HydroxideHCID 676694Methyl indole-7-carboxylateHCID 6327651Borane,N-dimethylmethanamine (1:1)

생성물 1

HCID 14072919Methyl 2,3-dihydro-1H-indole-7-carboxylate수율 71.2%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 312751,4-Dioxane용매

실험 절차

1.75 g of indole-7-carboxylic acid methyl ester and 2.92 g of borane-trimethylamine complex are dissolved in 10 ml of dioxane. To the resulting solution, 2 ml of concentrated hydrochloric acid are added. The reaction solution is heated under reflux for 30 minutes, and then cooled to room temperature. 10 ml of 6N hydrochloric acid are added to the reaction solution, which is then refluxed under heating for 15 minutes, and thereafter cooled to room temperature. The reaction solution is poured into 50 ml of water. The resulting mixture is neutralized with a 2N aqueous sodium hydroxide solution, and then extractd with ether. The organic layer is washed with a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. After the solvent has been distilled off, 1.26 g of 2,3-dihydroindole-7-carboxylic acid methyl ester are obtained, mp. 70° to 73° C.

후처리

  1. temperatureThe reaction solution is heated
  2. temperatureunder reflux for 30 minutes
  3. temperatureis then refluxed
  4. temperatureunder heating for 15 minutes
  5. temperaturecooled to room temperature
  6. washThe organic layer is washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationAfter the solvent has been distilled off

출처 및 근거

ORD 기록
ord-6e4da85376484ebdb25a60f35da2ad1d
출처 데이터셋
uspto-grants-1988_03
특허 번호
US04729998

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