Acetic Acid → HCID 15591134, compound

HRID 255647Notes

Reaction equation

HRID 255647 reaction equation
[NH:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20]([C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=3)=[CH:19][C:18](=[O:31])[C:13]([C:14]([O:16]C)=[O:15])=[CH:12]2)=[CH:7][CH:6]=1)C(C)=O.C(O)(=O)C>C(O)C.[OH-].[Na+].O>[NH2:1][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20]([C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=3)=[CH:19][C:18](=[O:31])[C:13]([C:14]([OH:16])=[O:15])=[CH:12]2)=[CH:7][CH:6]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 15590995HCID 15590995, compound

Product 1

HCID 15591134HCID 15591134, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

In a mixed solvent of 10 ml of ethanol and 10 ml of a 10% by weight aqueous sodium hydroxide solution was dissolved 0.5 g of methyl 1-(4-acetaminophenyl)-6-(2-naphthyl)-4-oxo-1,4-dihydronicotinate, and the solution was refluxed for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and diluted with 20 ml of water. This solution was then adjusted to a pH of 5.5 with acetic acid, and the precipitated crystals were collected by filtration, washed with water, and dried to obtain 0.38 g of 1-(4-aminophenyl)-6-(2-naphthyl)-4-oxo-1,4-dihydronicotinic acid having a melting point of 148°-151° C.

Workup

  1. temperaturethe solution was refluxed for 3 hours
  2. customAfter completion of the reaction
  3. filtrationthe precipitated crystals were collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-3dffd9ae84624075a3d4547a656a7360
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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