Potassium Carbonate → 3-Methyl-2-phenylquinoline

HRID 2308154Notes

Reaction equation

HRID 2308154 reaction equation
Cl[C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>COCCOC>[C:13]1([C:2]2[C:11]([CH3:12])=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 3390822-Chloro-3-methylquinoline

Product 1

HCID 14820143-Methyl-2-phenylquinolineYield 95.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Chloro-3-methylquinoline (5.43 g, 30.6 mmol), phenylboronic acid (4.47 g, 36.7 mmol), Pd(II) acetate (0.17 g, 0.76 mmol), and triphenylphosphine (0.80 g, 3.06 mmol) were dissolved in 100 mL DME. To the stirred solution was added K2CO3 (11.4 g dissolved into 41 mL H2O). The entire mixture was allowed to stir at reflux for 18 hours under N2 atmosphere. The cooled mixture was then removed of water, enriched with 150 mL of ethyl acetate, extracted three times from brine, dried over anhydrous sodium sulfate, filtered and evaporated of solvent. The crude liquid was then purified on a silica gel column using 20% ethyl acetate/hexanes. The purest fractions were combined to give 2-phenyl-3-methylquinoline (6.42 g, 95.8% yield).

Workup

  1. temperatureat reflux for 18 hours under N2 atmosphere
  2. customThe cooled mixture was then removed of water
  3. extractionextracted three times from brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated of solvent
  7. customThe crude liquid was then purified on a silica gel column

Sources & evidence

ORD record
ord-f88ef72012c34ea1b66348b72a15a306
Source dataset
uspto-grants-2004_12
Patent number
US06835469B2

Reaction notes

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