Methyl 2-phenyl-4-quinolinecarboxylate → 1-(2-Phenylquinolin-4-yl)ethanone

HRID 1597370Notes

Reaction equation

HRID 1597370 reaction equation
[C:1]1([C:7]2[CH:16]=[C:15]([C:17]([O:19]C)=O)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li][CH3:22]>CCOCC>[C:1]1([C:7]2[CH:16]=[C:15]([C:17](=[O:19])[CH3:22])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 609693Methyl 2-phenyl-4-quinolinecarboxylateHCID 178418348HCID 178418348, compound

Product 1

HCID 3441581-(2-Phenylquinolin-4-yl)ethanoneYield 24.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To methyl 2-phenyl-4-quinolinecarboxylate (1 g, 3.80 mmol) in 10 ml ether, at 0° C. was added MeLi (1.4M, 3.0 ml, 4.1 mmol) dropwise over a five minute period. The reaction mixture was stirred at 0° C. for 30 minutes and quenched by the addition of 10 ml of water. The ether layer was separated, dried over sodium sulfate, filtered, concentrated and purified (hexane:EtOAc; 4.5:0.5) to give 0.233 g (23%) of the product as a syrup which was used as such for the subsequent step.

Workup

  1. customquenched by the addition of 10 ml of water
  2. customThe ether layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified (hexane:EtOAc; 4.5:0.5)

Sources & evidence

ORD record
ord-28a1f66a716542b98f6f5a463d8cfb38
Source dataset
uspto-grants-2001_09
Patent number
US06294566B1

Reaction notes

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