Sodium Hydroxide → 3-[4-(4-Oxo-1,4-dihydropyridin-1-yl)benzoyl]butanoic acid

HRID 2231366Notes

Reaction equation

HRID 2231366 reaction equation
F[C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH:8]([CH3:13])[CH2:9][C:10]([OH:12])=[O:11])=[O:7])=[CH:4][CH:3]=1.[OH:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.[OH-].[Na+]>O>[O:16]=[C:17]1[CH:22]=[CH:21][N:20]([C:2]2[CH:15]=[CH:14][C:5]([C:6]([CH:8]([CH3:13])[CH2:9][C:10]([OH:12])=[O:11])=[O:7])=[CH:4][CH:3]=2)[CH:19]=[CH:18]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 124495243-(4-Fluorobenzoyl)butanoic acidHCID 178418642HCID 178418642, compound

Product 1

HCID 99477483-[4-(4-Oxo-1,4-dihydropyridin-1-yl)benzoyl]butanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 3-(4-fluorobenzoyl)butanoic acid (885 g), 4-hydroxypyridine (663 g) and sodium hydroxide (453 g) in water (2.2 liters) was stirred under reflux for 24 hours. The reaction mixture was cooled, diluted with water (10 liters) and filtered through diatomaceous earth. The filtrate was acidified to pH 3 with concentrated hydrochloric acid to afford as a cream solid 3-[4-(4-oxo-1,4-dihydropyridin-1-yl)benzoyl]butanoic acid, 1127 g (94%), m.p. 251°-254° C.

Workup

  1. temperatureunder reflux for 24 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through diatomaceous earth

Sources & evidence

ORD record
ord-9315b0928757414090e98232b2951f49
Source dataset
uspto-grants-1988_11
Patent number
US04782159

Reaction notes

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