Ethanol → Ethyl 6-hydroxyquinoline-2-carboxylate

HRID 493424Notes

Reaction equation

HRID 493424 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2.S(=O)(=O)(O)O.[CH2:20](O)[CH3:21]>>[CH2:20]([O:13][C:12]([C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([OH:1])[CH:3]=2)[N:8]=1)=[O:14])[CH3:21]

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 1118Sulfuric AcidHCID 133367806-Hydroxyquinoline-2-carboxylic acid

Product 1

HCID 57681568Ethyl 6-hydroxyquinoline-2-carboxylate

Procedure

6-Hydroxy-quinoline-2-carboxylic acid (2.3 g, 0.012 mol) was dissolved in absolute ethanol (150 ml). Sulfuric acid (0.550 ml, 0.0096 mol) was added and the mixture was refluxed for 16 hours. After cooling to room temperature the ethanol was evaporated and 60 ml of ethyl acetate, 50 ml of cooled water were added. The pH was adjusted to 7 with solid NaHCO3. Extraction and concentration of the organic phase gave the title product as a light yellow solid that was used for the next steps without purification (2.1 g, 81% of theory). MS (m/e)=218.4 (M+H)+.

Workup

  1. temperaturethe mixture was refluxed for 16 hours
  2. customwas evaporated
  3. addition60 ml of ethyl acetate, 50 ml of cooled water were added
  4. extractionExtraction and concentration of the organic phase

Sources & evidence

ORD record
ord-a9ed3583660647f3aa9bd5df695dae7e
Source dataset
uspto-grants-2009_05
Patent number
US07534891B2

Reaction notes

Loading…