Potassium Carbonate → 1-Phenylisoquinoline

HRID 7336

반응식

HRID 7336 반응식
Cl[N:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(COC)OC>[C:12]1([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:10]=[CH:11][N:2]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 219893902-Chloroisoquinoline

생성물 1

HCID 1378821-Phenylisoquinoline수율 96.9%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

2-Chloro-isoquinoline (28.8 g, 0.176 mol), phenylboronic acid (25.7 g 0.211 mol), triphenylphosphine (4.6 g 17.6 mmol), palladium acetate (0.99 g 4.4 mmol) and 2M solution of potassium carbonate (65.7 g 0.475 mol) were added to 270 ml of dimethoxyethane. This mixture was stirred at reflux for 17 hrs. The mixture was then cooled and the aqueous layer was separated from the organic layer. The aqueous extraction was then extracted with ethyl acetate. The combined organic extractions were then extracted with brine and dried over magnesium sulfate. The solvent was then evaporated to give a liquid which was then purified by Kugelhor distillation at 220° C. @1200 microns to yield 35 g (96.9%) of 1-phenylisoquinoline.

후처리

  1. temperatureat reflux for 17 hrs
  2. temperatureThe mixture was then cooled
  3. customthe aqueous layer was separated from the organic layer
  4. extractionThe aqueous extraction
  5. extractionwas then extracted with ethyl acetate
  6. extractionThe combined organic extractions
  7. extractionwere then extracted with brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was then evaporated
  10. customto give a liquid which
  11. distillationwas then purified by Kugelhor distillation at 220° C. @1200 microns

출처 및 근거

ORD 기록
ord-d9f85d7ffa8444e78678cc9498e7bd8a
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087321B2

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