Methanol → Methyl 4-methoxy-6-quinolinecarboxylate

HRID 1072875Notes

Reaction equation

HRID 1072875 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#N)[CH:10]=2)[N:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:15].[C:19](=O)([O-])[OH:20].[Na+].[CH3:24][OH:25]>>[CH3:24][O:25][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:20][CH3:19])=[O:15])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric Acid2×HCID 516892Sodium BicarbonateHCID 204935814-Chloroquinoline-6-carbonitrile

Product 1

HCID 22387888Methyl 4-methoxy-6-quinolinecarboxylate

Procedure

To a suspension of 4-chloro-6-quinolinecarbonitrile (910 mg) in methanol (50 ml) was dropwise added slowly concentrated sulfuric acid (5 ml) while stirring under ice-cooling. The mixture was heated under reflux for 15 hr and concentrated sulfuric acid (10 ml) was added. The mixture was further heated under reflux for 24 hr. An aqueous sodium hydrogencarbonate solution was added thereto under ice-cooling to make the reaction mixture basic. The reaction mixture was extracted once with chloroform. The organic layer was washed once with water and saturated brine, respectively, and dried over magnesium sulfate. The organic layer was concentrated to dryness under reduced pressure to give a white solid. The solid was pulverized by IPE to give the object compound (910 mg) as a white powder.

Workup

  1. temperaturecooling
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 15 hr
  4. temperatureThe mixture was further heated
  5. temperatureunder reflux for 24 hr
  6. temperatureunder ice-cooling
  7. extractionThe reaction mixture was extracted once with chloroform
  8. washThe organic layer was washed once with water and saturated brine
  9. dry with materialrespectively, and dried over magnesium sulfate
  10. concentrationThe organic layer was concentrated to dryness under reduced pressure
  11. customto give a white solid

Sources & evidence

ORD record
ord-7a3d306a2bc94f748b38df0f86cfde97
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

Loading…