Water → 6,7-Dimethyl-5-methoxy-1,2-dihydro-1h-indole

HRID 1743398노트

반응식

HRID 1743398 반응식
[CH3:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH2:6][C:7](=O)[NH:8]2)=[CH:4][C:3]=1[O:13][CH3:14].O>C1COCC1>[CH3:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH2:6][CH2:7][NH:8]2)=[CH:4][C:3]=1[O:13][CH3:14]

참가 물질

4

반응물 2

HCID 962WaterHCID 222380866,7-Dimethyl-5-methoxy-1,3-dihydro-2H-indole-2-one

생성물 1

HCID 222380716,7-Dimethyl-5-methoxy-1,2-dihydro-1h-indole수율 66%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

To a solution of 6,7-dimethyl-5-methoxy-1,3-dihydro-2H-indole-2-one (17.5 g, 91.5 mmol) in THF (500 mL) was added dropwise 1M-borane THF complex salt (306 mmol) at 0° C., and the mixture was stirred at 60° C. 3 hours. After ice-cooling, the mixture was added dropwise to water (100 mL). THF was distilled off under reduced pressure, concentrated hydrochloric acid (100 mL) was added, and the mixture was stirred under reflux for 2 hours. After neutralizing with 12N sodium hydroxide under ice-cooling, the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and purified by small amount silica gel column chromatography (ethyl acetate). The solvent was distilled off under reduced pressure, followed by recrystallization from hexane, to obtain 8.18 g of the title compound.

후처리

  1. custom3 hours
  2. temperatureAfter ice-cooling
  3. distillationTHF was distilled off under reduced pressure, concentrated hydrochloric acid (100 mL)
  4. additionwas added
  5. stirringthe mixture was stirred
  6. temperatureunder reflux for 2 hours
  7. temperaturecooling
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over sodium sulfate
  11. custompurified by small amount silica gel column chromatography (ethyl acetate)
  12. distillationThe solvent was distilled off under reduced pressure
  13. customfollowed by recrystallization from hexane

출처 및 근거

ORD 기록
ord-f231fb87325e4d3f9cf62be08a9c2d3b
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07008940B1

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