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Potassium Hydroxide → 5-Bromo-3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline

HRID 1477112
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HRID 1477112 반응식
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][C:5]([CH3:17])([CH3:16])[N:6](C(OC)=O)[CH2:7]2.[OH-].[K+]>C(O)CO.O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][C:5]([CH3:17])([CH3:16])[NH:6][CH2:7]2
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참가 물질

5

반응물 2

HCID 14797Potassium HydroxideHCID 89500998HCID 89500998, 화합물

생성물 1

HCID 846296205-Bromo-3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline수율 40.5%

시약·촉매·용매 2

HCID 174Ethylene Glycol용매HCID 962Water용매

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온도
150 °C

실험 절차

To a solution of Intermediate 6E (4.6 g) in ethylene glycol (50 mL) was added 50% aqueous KOH solution (23 mL) and the reaction was heated at 150° C. for 3 days. The reaction mixture was cooled, diluted with H2O, extracted with EtOAc twice. The combined organics were extracted with 1.5 N HCl solution, the aqueous layer was basified with 10% NaOH solution, extracted with EtOAc twice and the combined organics were washed with H2O, brine, dried over Na2SO4, filtered and concentrated to give Intermediate 6F (1.5 g, 39.4%) as a brown liquid. MS (ESI) m/z: 242.2 (M+H)+.

후처리

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with EtOAc twice
  3. extractionThe combined organics were extracted with 1.5 N HCl solution
  4. extractionextracted with EtOAc twice
  5. washthe combined organics were washed with H2O, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f56885cc9421496b9d1695bedaaa99c6
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09403774B2

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