Potassium Hydroxide → 3,3-Dimethyl-3,4-dihydroisoquinoline

HRID 2393762노트

반응식

HRID 2393762 반응식
[OH-].[K+].C1(C)C(S([N:12]2[C:21]([CH3:23])([CH3:22])[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13]2)(=O)=O)=CC=CC=1>CO>[CH3:22][C:21]1([CH3:23])[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[N:12]1

참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 18977225HCID 18977225, 화합물

생성물 1

HCID 110409823,3-Dimethyl-3,4-dihydroisoquinoline수율 90%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a nitrogen-blanketed mixture of potassium hydroxide (KOH, 30 g) and methanol (CH3OH, 60 mL) was added of N-toluenesulfonyl-3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline (4.0 g, 0.013 mol.). The reaction mixture was heated at reflux for 17 hours and the reaction was followed by gas chromatography. The reaction mixture was cooled to ambient temperature, quenched with water (100 mL) and 10% HCl was slowly added until pH=7 was obtained. The aqueous mixture was extracted with methylene chloride (3×100 mL) and the organic layers were combined and stirred with charcoal and sodium sulfate (Na2 SO4). The solution was filtered through celite and the filtrate was concentrated (25°/150 torr) to give 3,3-dimethyl-3,4-dihydroisoquinoline (1.79 g, yield=90%).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 17 hours
  3. customquenched with water (100 mL) and 10% HCl
  4. additionwas slowly added until pH=7
  5. customwas obtained
  6. extractionThe aqueous mixture was extracted with methylene chloride (3×100 mL)
  7. filtrationThe solution was filtered through celite
  8. concentrationthe filtrate was concentrated (25°/150 torr)

출처 및 근거

ORD 기록
ord-cfb4ba39b8be4522a3697d04ebf8f1bf
출처 데이터셋
uspto-grants-1998_09
특허 번호
US05808071

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