Quinoline → 2-Phenylquinoline

HRID 2292116Notes

Reaction equation

HRID 2292116 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:11]1([Li])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CCOCC>[C:11]1([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 7047Quinoline2×HCID 178506676HCID 178506676, compound

Product 1

HCID 715452-Phenylquinoline

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Quinoline (40 g) was dissolved in dry ether (250 ml) and treated dropwise with a solution of phenyl lithium (160 ml of 1.88 m solution in benzene/ether). The mixture was stirred at room temperature for 18 hr., then washed with aqueous ammonium chloride solution (20% w/v 2×100 ml) and then water (2×100 ml). The aqueous phase was extracted with ether (2×100 ml) and the combined ether layers were dried (magnesium sulphate) and evaporated in vacuo to give an oil. Unreacted quinoline was removed from the product by distillation in vacuo (80°-90°/10-15 mm Hg). A portion of the residue was crystallised from industrial methylated spirit to afford 2-phenylquinoline m.pt. 84°-86° characterised by its nmr spectrum. The bulk of the product was also characterised by its nmr spectrum.

Workup

  1. wash, then washed with aqueous ammonium chloride solution (20% w/v 2×100 ml)
  2. extractionThe aqueous phase was extracted with ether (2×100 ml)
  3. dry with materialthe combined ether layers were dried (magnesium sulphate)
  4. customevaporated in vacuo
  5. customto give an oil
  6. customwas removed from the product by distillation in vacuo (80°-90°/10-15 mm Hg)
  7. customA portion of the residue was crystallised from industrial methylated spirit

Sources & evidence

ORD record
ord-dd0f3f7f89dd490d8e6657a5e44a1ef5
Source dataset
uspto-grants-1989_01
Patent number
US04801593

Reaction notes

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