Ethanol → 6-Quinolinecarboxylic acid, ethyl ester

HRID 537150Notes

Reaction equation

HRID 537150 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.S(=O)(=O)(O)O.[CH2:19](O)[CH3:20]>C(OCC)(=O)C>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH2:19][CH3:20])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 825716-Quinolinecarboxylic acid

Product 1

HCID 946706-Quinolinecarboxylic acid, ethyl esterYield 81%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of quinoline-6-carboxylic acid (2.8 g, 16 mmol) in ethanol (100 mL) was added concentrated sulfuric acid (2 mL). The reaction was heated to reflux overnight. The solvent was evaporated to give a brown residue that was taken up in ethyl acetate (150 mL). The mixture was washed with water (2×30 mL), saturated aqueous sodium bicarbonate (2×30 mL), and brine (2×30 mL). The organic layer was dried over sodium sulphate, filtered, and concentrated to an oil. Purification by flash column chromatography gave the title compound (2.0 g, 81%) as a brown solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. customThe solvent was evaporated
  4. customto give a brown residue that
  5. washThe mixture was washed with water (2×30 mL), saturated aqueous sodium bicarbonate (2×30 mL), and brine (2×30 mL)
  6. dry with materialThe organic layer was dried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to an oil
  9. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-4574ccd60edc463c887a71f070f1ceae
Source dataset
uspto-grants-2014_10
Patent number
US08859773B2

Reaction notes

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