Potassium Carbonate → 1-Phenylisoquinoline

HRID 2117246Notes

Reaction equation

HRID 2117246 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)CO.COC>[C:12]1([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[CH:4][N:3]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 140539Isoquinoline, 1-chloro-

Product 1

HCID 1378821-PhenylisoquinolineYield 90%

Reagents, catalysts & solvents 1

HCID 21863332Dimethyl ether ethylene glycolSolvent

Conditions

Temperature
90 °C

Procedure

3.0 g of 1-chloro-isoquinoline (18 mmmol), 2.7 g of Phenyl boronic acid (21 mmol), 1.6 g of tetrakis-triphenylphosphine palladium (0.8 mmol %), and 2.9 g of potassium carbonate (21 mmol) were added into 100 ml of reaction bowl, and 50 ml of ethylene glycol-dimethyl ether as distilled solvent was added thereto under the flow of nitrogen, and then the reaction was performed in reflux at 90° C. for 12 hr. The mixture was cooled to room temperature, extracted by chloroform and distilled water, and then, separated by silica gel column chromatography (chloroform:hexane=1:3), to obtain 3.32 g of 1-phenyl-isoquinoline (yield: 90%).

Workup

  1. distillationas distilled solvent
  2. additionwas added
  3. temperatureThe mixture was cooled to room temperature
  4. extractionextracted by chloroform
  5. distillationdistilled water
  6. customseparated by silica gel column chromatography (chloroform:hexane=1:3)

Sources & evidence

ORD record
ord-9f8c8816ff8448408184d0b77f719359
Source dataset
uspto-grants-2008_10
Patent number
US07442448B2

Reaction notes

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