Sodium Hydroxide → HCID 22116092, compound

HRID 1942515Notes

Reaction equation

HRID 1942515 reaction equation
[C:1]1([C:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][C:8]=2[C:20]([O:22]CC)=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[C:16]([O:15][C:13]([N:10]1[CH2:11][CH2:12][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:8]([C:20]([OH:22])=[O:21])[CH2:9]1)=[O:14])([CH3:19])([CH3:17])[CH3:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59234224HCID 59234224, compound

Product 1

HCID 22116092HCID 22116092, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-tert-Butyl 3-ethyl 4-phenyl-5,6-dihydropyridin-1,3(2H)-dicarboxylate (7.07 g) was dissolved in ethanol (50 ml), and thereto was added 1M aqueous sodium hydroxide solution (50 ml), and the mixture was refluxed for 2 hours. The reaction solution was concentrated under reduced pressure, and thereto was added 1M aqueous sodium hydroxide solution and ethyl acetate for separation. To the organic layer was added 1M aqueous sodium hydroxide solution for separation, and the aqueous layers were combined, and the pH value thereof was adjusted to pH<2 by the addition of 2M hydrochloric acid. The mixture was extracted with chloroform, and the organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound (5.63 g).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionwas added 1M aqueous sodium hydroxide solution and ethyl acetate
  4. customfor separation
  5. additionTo the organic layer was added 1M aqueous sodium hydroxide solution
  6. customfor separation
  7. additionthe pH value thereof was adjusted to pH<2 by the addition of 2M hydrochloric acid
  8. extractionThe mixture was extracted with chloroform
  9. dry with materialthe organic layer was dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f4083fed545f4d3bba541e2b094b09f2
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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