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

HRID 2231365Notes

Reaction equation

HRID 2231365 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+].Cl>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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 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 962WaterSolvent

Procedure

A solution of 3-(4-fluorobenzoyl)butanoic acid (8 g), 4-hydroxypyridine (8 g) and sodium hydroxide (4.6 g) in water (80 ml) was heated in an autoclave at 140° C. for 20 hours. The reaction mixture was cooled and was acidified to pH 3-4 with dilute hydrochloric acid to afford as a white crystalline precipitate 3-[4-(4-oxo-1,4-dihydropyridin-1-yl)benzoyl]butanoic acid, 9.45 g (87%), m.p. 250°-252° C.

Workup

  1. temperatureThe reaction mixture was cooled

Sources & evidence

ORD record
ord-4755cf1877ce41d5894f9c5b9f016f55
Source dataset
uspto-grants-1988_11
Patent number
US04782159

Reaction notes

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