Sodium Carbonate → 4-(4'-Chloro-2'-fluoro-biphenyl-4-yl)-4-hydroxyimino-butyric acid

HRID 1979149Notes

Reaction equation

HRID 1979149 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=O)[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)=[C:4]([F:21])[CH:3]=1.Cl.[NH2:23][OH:24].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[N:23][OH:24])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)=[C:4]([F:21])[CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 183641244-(2'-Fluoro-4'-chloro-4-biphenylyl)-4-oxo-butyric acid

Product 1

HCID 734323224-(4'-Chloro-2'-fluoro-biphenyl-4-yl)-4-hydroxyimino-butyric acidYield 85.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a manner similar to Example 4, Step (c), 4-(4′-chloro-2′-fluoro-biphenyl-4-yl)-4-oxo-butyric acid (1.100 g, 0.00359 mol) was allowed to react with hydroxylamine hydrochloride (0.300 g, 0.00432 mol) in the presence of sodium carbonate (0.458 g, 0.00432 mol) in absolute ethanol (20 mL) to give 0.989 g of 4-(4′-chloro-2′-fluoro-biphenyl-4-yl)-4-hydroxyimino-butyric acid as an off-white solid; mp 147.5-149.5° C.

Sources & evidence

ORD record
ord-10980d4e61b04546aadea6d0daf73a73
Source dataset
uspto-grants-2001_05
Patent number
US06239288B1

Reaction notes

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