Phosphate → HCID 59377698, compound

HRID 1691778Notes

Reaction equation

HRID 1691778 reaction equation
C([N:9]1[CH:14]=[CH:13][C:12](=[O:15])[CH2:11][CH:10]1[C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[C:19]#[N:20])(=O)C1C=CC=CC=1.C[O-].[Na+].P([O-])([O-])([O-])=O>CO>[C:19]([C:18]1[CH:17]=[C:16]([CH:10]2[CH2:11][C:12](=[O:15])[CH:13]=[CH:14][NH:9]2)[CH:23]=[CH:22][CH:21]=1)#[N:20]

Participants

5

Reactant 3

HCID 1061PhosphateHCID 10942334Sodium MethoxideHCID 59377683HCID 59377683, compound

Product 1

HCID 59377698HCID 59377698, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

3-(1-Benzoyl-4-oxo-1,2,3,4-tetrahydro-pyridin-2-yl)-benzonitrile (350 mg) was dissolved in 50 ml methanol at 0° C. and 1.5 ml of 0.5 M sodium methoxide in methanol was added. The solution was stirred at 0° C. for 3 hours, and then 25 ml of pH 7 phosphate buffer was added. The mixture was concentrated under reduced pressure and partitioned between buffer and ethyl acetate. The organic layer was dried over sodium sulfate and the drying agent filtered off. Racemic 2-(3-cyanophenyl)-2,3-dihydro-pyridin-4-one was crystallized by addition of hexane to give 131 mg.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. custompartitioned between buffer and ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationthe drying agent filtered off
  5. customRacemic 2-(3-cyanophenyl)-2,3-dihydro-pyridin-4-one was crystallized by addition of hexane
  6. customto give 131 mg

Sources & evidence

ORD record
ord-796f3b29561345c083bbf688f3759b9a
Source dataset
uspto-grants-2012_04
Patent number
US08153808B2

Reaction notes

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