Potassium Carbonate → 1-Phenylisoquinoline

HRID 7336

Reaction equation

HRID 7336 reaction equation
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

Participants

7

Reactant 4

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

Product 1

HCID 1378821-PhenylisoquinolineYield 96.9%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d9f85d7ffa8444e78678cc9498e7bd8a
Source dataset
uspto-grants-2006_08
Patent number
US07087321B2

Linked notes

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