Hydrochloric Acid → 2-Benzyl-7-ethoxycarbonyl-3-hydroxyquinoline

HRID 1359421Notes

Reaction equation

HRID 1359421 reaction equation
[CH2:1]([C:8]1[C:17]([OH:18])=[CH:16][C:15]2[C:10](=[CH:11][C:12]([C:19]#N)=[CH:13][CH:14]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:21].[K+].O.Cl.[CH2:25]([OH:27])[CH3:26]>>[CH2:1]([C:8]1[C:17]([OH:18])=[CH:16][C:15]2[C:10](=[CH:11][C:12]([C:19]([O:27][CH2:25][CH3:26])=[O:21])=[CH:13][CH:14]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 14797Potassium HydroxideHCID 181822382-Benzyl-7-cyano-3-hydroxyquinoline

Product 1

HCID 181822522-Benzyl-7-ethoxycarbonyl-3-hydroxyquinoline

Procedure

A mixture of 203 mg of 2-benzyl-7-cyano-3-hydroxyquinoline, 2.6 g of potassium hydroxide, 5.5 ml of water and 20 ml of ethanol was heated under reflux for 2 hours. After cooling as it was, dilute hydrochloric acid was added thereto. The mixture was extracted with diethyl ether and the solvent was removed. To the residue were added 30 ml of ethanol and 3.0 ml of concentrated sulfuric acid, followed by heating under reflux for one hour. After cooling as it was, the solvent was removed. Diethyl ether and an aqueous potassium carbonate solution were added thereto, followed by extracting with diethyl ether. The organic phase was washed with brine and the solvent was removed, to give 204 mg of the target compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling as it
  4. extractionThe mixture was extracted with diethyl ether
  5. customthe solvent was removed
  6. additionTo the residue were added 30 ml of ethanol and 3.0 ml of concentrated sulfuric acid
  7. temperatureby heating
  8. temperatureunder reflux for one hour
  9. temperatureAfter cooling as it
  10. customthe solvent was removed
  11. additionDiethyl ether and an aqueous potassium carbonate solution were added
  12. extractionby extracting with diethyl ether
  13. washThe organic phase was washed with brine
  14. customthe solvent was removed

Sources & evidence

ORD record
ord-821c6393e0444f4fbeed3a98e1d67ab7
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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