Potassium Sodium Tartrate → HCID 66884704, compound

HRID 1801631Notes

Reaction equation

HRID 1801631 reaction equation
C[O:2][C:3](=O)[CH:4]([CH3:19])[CH2:5][CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][C:14](=[O:18])[NH:15]2)=[CH:10][CH:9]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>O1CCCC1>[OH:2][CH2:3][CH:4]([CH3:19])[CH2:5][CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][C:14](=[O:18])[NH:15]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 66884880HCID 66884880, compound

Product 1

HCID 66884704HCID 66884704, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6 g of 2-methyl-4-(2-oxo-1,2,3,4-tetrahydroquinolin-7-yloxy)butyric acid methyl ester was added dropwise to a tetrahydrofuran (200 ml) suspension of 1.6 g of lithium aluminum hydride while being stirred under ice-cooling and stirred at the same temperature for 2 hours. While being stirred under ice-cooling, saturated Rochelle salt aqueous solution was added, which was extracted with diethyl ether and, after washed with water, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:methanol=40:1), and 2.8 g of 7-(4-hydroxy-3-methylbutoxy)-3,4-dihydro-1H-quinolin-2-one was obtained in the form of a yellow oil.

Workup

  1. temperaturecooling
  2. stirringstirred at the same temperature for 2 hours
  3. stirringWhile being stirred under ice-
  4. temperaturecooling
  5. extractionwhich was extracted with diethyl ether
  6. washafter washed with water
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=40:1)

Sources & evidence

ORD record
ord-c5dd30706ce74243b2e43d3547cddc2b
Source dataset
uspto-grants-2013_01
Patent number
US08349840B2

Reaction notes

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