Methanol → Methyl quinoline-4-carboxylate

HRID 2187355

Reaction equation

HRID 2187355 reaction equation
S(Cl)(Cl)=O.[N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]([OH:17])=[O:16])=[CH:7][CH:6]=1.[CH3:18]O>>[N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]([O:17][CH3:18])=[O:16])=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 102434-Quinolinecarboxylic acidHCID 24386Thionyl Chloride

Product 1

HCID 3002895Methyl quinoline-4-carboxylateYield 42%

Conditions

Temperature
-2.5 °C

Procedure

Thionyl chloride (4.5 ml) was added dropwise, under argon to a cooled, stirring slurry of 4-quinolinecarboxylic acid (5.32 g) in methanol (120 ml) maintaining an internal temperature of 0 to −5° C. Once addition was complete the reaction mixture was heated at reflux for 16 h. After cooling to ambient temperature the volatiles were removed at reduced pressure and the residue partitioned between saturated aqueous sodium bicarbonate and diethyl ether. The organic phase was washed with brine, dried (Na2SO4) and the solvent removed at reduced pressure to give the title compound as a pale yellow oil (4.82 g).

Workup

  1. additionOnce addition
  2. temperaturewas heated
  3. temperatureat reflux for 16 h
  4. temperatureAfter cooling to ambient temperature the volatiles
  5. customwere removed at reduced pressure
  6. customthe residue partitioned between saturated aqueous sodium bicarbonate and diethyl ether
  7. washThe organic phase was washed with brine
  8. dry with materialdried (Na2SO4)
  9. customthe solvent removed at reduced pressure

Sources & evidence

ORD record
ord-55adacad8aad49a78e6ae095e2e58d6f
Source dataset
uspto-grants-2002_06
Patent number
US06410529B1

Linked notes

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