Hydroxyamine hydrochloride → 5-[(E)-C-[2-(4-chloro-2-methylphenyl)-2-(3-fluoro-4-hydroxyphenyl)ethyl]-N-hydroxycarbonimidoyl]-1-methylpyridin-2-one

HRID 1617890Notes

Reaction equation

HRID 1617890 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([F:27])[CH:21]=2)[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)=O)=[C:4]([CH3:28])[CH:3]=1.Cl.[NH2:30][OH:31].C(=O)([O-])O.[Na+]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([F:27])[CH:21]=2)[CH2:9]/[C:10](/[C:12]2[CH:13]=[CH:14][C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)=[N:30]\[OH:31])=[C:4]([CH3:28])[CH:3]=1

Participants

4

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 666691835-[3-(4-Chloro-2-methyl-phenyl)-3-(3-fluoro-4-hydroxy-phenyl)-propionyl]-1-methyl-1H-pyridin-2-one

Product 1

HCID 580436015-[(E)-C-[2-(4-chloro-2-methylphenyl)-2-(3-fluoro-4-hydroxyphenyl)ethyl]-N-hydroxycarbonimidoyl]-1-methylpyridin-2-one

Procedure

In analogy to example 151, step 3, 5-[3-(4-chloro-2-methyl-phenyl)-3-(3-fluoro-4-hydroxy-phenyl)-propionyl]-1-methyl-1H-pyridin-2-one was reacted with hydroxylamine hydrochloride in the presence of sodium hydrogencarbonate to give the title compound containing <5% of the corresponding Z isomer as a colourless solid, MS (ESI−): m/z=413.0 [M−H]−.

Sources & evidence

ORD record
ord-b82bbefeb0a749b98979980576a21739
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

Loading…