Ethanol → HCID 66880713, compound

HRID 1893555Notes

Reaction equation

HRID 1893555 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[C:13]([OH:15])=[O:14].S(=O)(=O)(O)O.[CH2:21](O)[CH3:22]>>[CH2:21]([O:14][C:13]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[CH3:1])[NH:9][C:8](=[O:12])[CH2:7][CH2:6]2)=[O:15])[CH3:22]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 109656417-Methyl-2-oxo-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

Product 1

HCID 66880713HCID 66880713, compoundYield 70%

Procedure

To the compound (40.0 g, 195 mmol) obtained in step A were added ethanol (600 ml) and concentrated sulfuric acid (60 ml), and the mixture was heated under reflux for 24 hr. After cooling to room temperature, the solution was concentrated under reduced pressure. The obtained oil was diluted with water, and extracted with chloroform. The organic layer was washed with diluted aqueous sodium hydroxide solution, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained solid was recrystallized from ethanol to give the title compound (32.0 g, yield 70%) as a colorless solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hr
  3. concentrationthe solution was concentrated under reduced pressure
  4. additionThe obtained oil was diluted with water
  5. extractionextracted with chloroform
  6. washThe organic layer was washed with diluted aqueous sodium hydroxide solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe insoluble material was filtered off
  9. concentrationthe solution was concentrated under reduced pressure
  10. customThe obtained solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-c6ed2e7ab3104c518d9156f996b2db24
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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