Hydrochloric Acid → 4-methoxy-2,3-dihydro-1H-indole

HRID 430779노트

반응식

HRID 430779 반응식
[B-][N+](C)(C)C.Cl.[CH3:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2>O1CCOCC1>[CH3:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][CH2:12][NH:13]2

참가 물질

5

반응물 3

HCID 313Hydrochloric Acid2회HCID 1383634-Methoxy-1H-indoleHCID 6327651Borane,N-dimethylmethanamine (1:1)

생성물 1

HCID 162444414-methoxy-2,3-dihydro-1H-indole수율 83%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

Borane-trimethylamine complex (3.00 g) and 10.5N hydrochloric acid (2.25 ml) were added to 4-methoxyindole (1.29 g) in dioxane (20 ml), and the mixture was heated to reflux for 30 minutes. To this mixture, 6N hydrochloric acid (7.00 ml) was added and the mixture was heated to reflux for 15 minutes. The solvent was removed under reduced pressure and 1N aqueous sodium hydroxide solution was added to change the aqueous layer to alkaline condition, followed by extracting the aqueous layer with ether (3×20 ml). The obtained organic layers were washed with saturated brine and dried over sodium sulfate. After removing solids by filtration, the solvent was removed under reduced pressure, and the obtained crude product was purified by silica gel column chromatography to obtain the desired compound (1.08 g, yield: 83%).

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 30 minutes
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 15 minutes
  5. customThe solvent was removed under reduced pressure and 1N aqueous sodium hydroxide solution
  6. additionwas added
  7. extractionby extracting the aqueous layer with ether (3×20 ml)
  8. washThe obtained organic layers were washed with saturated brine
  9. dry with materialdried over sodium sulfate
  10. customAfter removing solids
  11. filtrationby filtration
  12. customthe solvent was removed under reduced pressure
  13. customthe obtained crude product
  14. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-cc3004f1dd034e4c8e56fa2c8decc2a1
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06323235B1

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