Hydrochloric Acid → 4-(1-Methyl-4-oxo-1,4-dihydropyridin-3-yl)benzoic acid

HRID 910608Notes

Reaction equation

HRID 910608 reaction equation
[OH-].[Na+].[CH3:3][N:4]1[CH:9]=[CH:8][C:7](=[O:10])[C:6]([C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=[O:16])=[CH:13][CH:12]=2)=[CH:5]1.Cl>CCO>[CH3:3][N:4]1[CH:9]=[CH:8][C:7](=[O:10])[C:6]([C:11]2[CH:20]=[CH:19][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=2)=[CH:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57583987Methyl 4-(1-methyl-4-oxo-1,4-dihydropyridin-3-yl)benzoate

Product 1

HCID 575840694-(1-Methyl-4-oxo-1,4-dihydropyridin-3-yl)benzoic acidYield 84.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1 M NaOH (1.42 ml) was added to an EtOH suspension (3 ml) of methyl 4-(1-methyl-4-oxo-1,4-dihydropyridin-3-yl)benzoate (115 mg), followed by stirring at room temperature for 8 hours. 1 M HCl (1.42 ml) was added to the reaction solution, followed by concentration under reduced pressure. Water (20 ml) was added to the residue, followed by stirring for 20 minutes. The precipitate formed was collected by filtration and dried under reduced pressure at 60° C. to obtain 4-(1-methyl-4-oxo-1,4-dihydropyridin-3-yl)benzoic acid (92 mg).

Workup

  1. concentrationfollowed by concentration under reduced pressure
  2. additionWater (20 ml) was added to the residue
  3. stirringby stirring for 20 minutes
  4. customThe precipitate formed
  5. filtrationwas collected by filtration
  6. customdried under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-93825d8b1fd04ca68dd31dbe8ae0f235
Source dataset
uspto-grants-2011_09
Patent number
US08022208B2

Reaction notes

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