1,2-Dimethoxyethane → 1-Phenylisoquinoline

HRID 2308155Notes

Reaction equation

HRID 2308155 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.COCCOC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(OCC)(=O)C>[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

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 140539Isoquinoline, 1-chloro-

Product 1

HCID 1378821-PhenylisoquinolineYield 81.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-Chloroisoquinoline (5.0 g, 30 mmol) and phenylboronic acid (4.5 g, 37 mmol) was dissolved into 100 mL of ethylene glycol dimethyl ether, followed by the addition of triphenylphosphine (0.7 g, 3 mmol) and Pd(II) acetate (0.17 g, 0.75 mmol). The reaction mixture was refluxed for 16 hours. The reaction mixture was cooled and the aqueous layer discarded. Additional ethyl acetate was added and the solvent was washed with a saturated solution of sodium chloride, dried over magnesium sulfate and concentrated to give 1-phenylisoquinoline (5.0 g, 79% yield)

Workup

  1. temperatureThe reaction mixture was refluxed for 16 hours
  2. temperatureThe reaction mixture was cooled
  3. washthe solvent was washed with a saturated solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-76acae5d57fd4ac8bf59e8bc29163c48
Source dataset
uspto-grants-2004_12
Patent number
US06835469B2

Reaction notes

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