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

HRID 381830Notes

Reaction equation

HRID 381830 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-8d3d5762f3724840a661e0278a44f5d6
Source dataset
uspto-grants-2001_10
Patent number
US06307089B2

Reaction notes

Loading…