Potassium Hydroxide → (E)-3-[1,4-Dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinyl]-2-propenoic acid

HRID 4117Notes

Reaction equation

HRID 4117 reaction equation
[O:1]=[C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][NH:5][C:4](/[CH:16]=[CH:17]/[C:18]([O:20]CC)=[O:19])=[CH:3]1.[OH-].[K+]>C(O)C>[O:1]=[C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][NH:5][C:4](/[CH:16]=[CH:17]/[C:18]([OH:20])=[O:19])=[CH:3]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 14182518(E)-3-[1,4-Dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinyl]-2-propenoic acid, ethyl ester

Product 1

HCID 14182519(E)-3-[1,4-Dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinyl]-2-propenoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(E)-3-[1,4-Dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinyl]-2-propenoic acid, ethyl ester (1.5 g) and 0.29 g of potassium hydroxide were stirred in 30 ml of ethanol for two hours at 50° C. After evaporating the solvent, the residue was dissolved in 100 ml of water and filtered. Hydrochloric acid (2N) was added to the filtrate until pH 5 was reached; crystals of the title compound separated. The crystals were filtered and washed with water and dried in vacuo (yield: 1.14 g).

Workup

  1. customAfter evaporating the solvent
  2. dissolutionthe residue was dissolved in 100 ml of water
  3. filtrationfiltered
  4. additionHydrochloric acid (2N) was added to the filtrate until pH 5
  5. customcrystals of the title compound separated
  6. filtrationThe crystals were filtered
  7. washwashed with water
  8. customdried in vacuo (yield: 1.14 g)

Sources & evidence

ORD record
ord-fae1bc17779a4c33ab6bacd79ee3ea5d
Source dataset
uspto-grants-1988_02
Patent number
US04723002

Reaction notes

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