Methanol → methyl quinoline-2-carboxylate

HRID 539648Notes

Reaction equation

HRID 539648 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=[O:12].S(Cl)(Cl)=O.[CH3:18]O>>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([O:13][CH3:18])=[O:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 7124Quinaldic AcidHCID 24386Thionyl Chloride

Product 1

HCID 421738methyl quinoline-2-carboxylate

Procedure

To an ice-cooled solution of quinoline-2-carboxylic acid 3.1 (10 g, 0.0578 mol) in 100 mL of absolute methanol was added dropwise thionyl chloride (20 g, 0.173 mol). After the addition was completed, the mixture was heated to reflux for 2 h. The solvent was then evaporated to dryness under reduced pressure and treated with 100 mL of 10% aqueous solution of K2CO3. The mixture was extracted with ethyl acetate; combined organic extracts were dried over sodium sulfate and evaporated to dryness to afford of methyl quinoline-2-carboxylate. Yield: 10.1 g (93%).

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 2 h
  4. customThe solvent was then evaporated to dryness under reduced pressure
  5. additiontreated with 100 mL of 10% aqueous solution of K2CO3
  6. extractionThe mixture was extracted with ethyl acetate
  7. dry with materialcombined organic extracts were dried over sodium sulfate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-564b9d80356248a99657f8006a773f83
Source dataset
uspto-grants-2014_10
Patent number
US08871761B2

Reaction notes

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