Hydrochloric Acid → Methyl quinoline-6-carboxylate

HRID 509338Notes

Reaction equation

HRID 509338 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.[CH3:15]O>>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:15])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 825716-Quinolinecarboxylic acid

Product 1

HCID 736812Methyl quinoline-6-carboxylate

Procedure

To a solution of quinoline-6-carboxylic acid (1.00 g, 5.77 mmol) in MeOH (10 mL) was added hydrogen chloride (2.00 mL, 8.00 mmol) (4.0M in 1,4-dioxane). The reaction was stirred 18 h at rt, LCMS shows <10% conversion. Additional hydrogen chloride (2.00 mL, 8.00 mmol) was added and the reaction heated to 50° C. in an oil bath 36 h. The reaction was cooled to rt and concentrated in vacuo. The solid was dissolved in DCM and extracted with sat. aqueous NaHCO3 (2×50 mL). The organic layer was dried (MgSO4), and concentrated to give the product which was used without further purification in the next step.

Workup

  1. temperaturethe reaction heated to 50° C. in an oil bath 36 h
  2. temperatureThe reaction was cooled to rt
  3. concentrationconcentrated in vacuo
  4. dissolutionThe solid was dissolved in DCM
  5. extractionextracted with sat. aqueous NaHCO3 (2×50 mL)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. concentrationconcentrated
  8. customto give the product which
  9. customwas used without further purification in the next step

Sources & evidence

ORD record
ord-572b84b0d9f84e90b9f55f0665a63145
Source dataset
uspto-grants-2015_08
Patent number
US09096527B2

Reaction notes

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