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Water → 4-(4-Chlorophenyl)-1,2-dimethyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acid

HRID 734723
Notes
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Reaction equation

HRID 734723 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[N:11]([CH3:15])[C:10]([CH3:16])=[C:9]2[C:17]([O:19]C)=[O:18])=[CH:4][CH:3]=1.[OH-].[Na+].O.CCOC(C)=O>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[N:11]([CH3:15])[C:10]([CH3:16])=[C:9]2[C:17]([OH:19])=[O:18])=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 5306292HCID 5306292, compound

Product 1

HCID 688301204-(4-Chlorophenyl)-1,2-dimethyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acidYield 75%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Conditions

Temperature
60 °C

Procedure

The product from step 1 (470 mg, 1.6 mmol, 1.0 equiv) was dissolved in MeOH (10 mL) and 2.5 M NaOH (2.5 mL) was added. The mixture was heated to 60° C. for three hours. When the reaction had cooled to room temperature, water and EtOAc were added. The phases were separated, and the aqueous layer was adjusted to pH 7 with 6N HCl. The aqueous phase was extracted with ethyl acetate. The organic extracts were dried over Na2SO4 and concentrated to dryness. The residue was azeotroped with hexanes to provide 335 mg (75%) of the title compound as a foamy white solid. MS (ES+) m/e 280 [M+H]+.

Workup

  1. temperatureWhen the reaction had cooled to room temperature
  2. customThe phases were separated
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe organic extracts were dried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customThe residue was azeotroped with hexanes

Sources & evidence

ORD record
ord-6e99dfa51ec84068b054fe533709d1a1
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07592357B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes