Hydroxyamine hydrochloride → 5-[(E)-C-[2-(4-chloro-2-methylphenyl)-2-(4-methylsulfonylphenyl)ethyl]-N-hydroxycarbonimidoyl]-1-(2-hydroxyethyl)pyridin-2-one

HRID 1617924Notes

Reaction equation

HRID 1617924 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=2)[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:21])[N:16]([CH2:18][CH2:19][OH:20])[CH:17]=2)=O)=[C:4]([CH3:32])[CH:3]=1.Cl.[NH2:34][OH:35].C(=O)([O-])O.[Na+]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=2)[CH2:9]/[C:10](/[C:12]2[CH:13]=[CH:14][C:15](=[O:21])[N:16]([CH2:18][CH2:19][OH:20])[CH:17]=2)=[N:34]\[OH:35])=[C:4]([CH3:32])[CH:3]=1

Participants

4

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 666690445-(3-(4-Chloro-2-methylphenyl)-3-(4-(methylsulfonyl)phenyl)propanoyl)-1-(2-hydroxyethyl)pyridin-2(1H)-one

Product 1

HCID 580433725-[(E)-C-[2-(4-chloro-2-methylphenyl)-2-(4-methylsulfonylphenyl)ethyl]-N-hydroxycarbonimidoyl]-1-(2-hydroxyethyl)pyridin-2-one

Procedure

In analogy to example 151, step 3, 5-(3-(4-chloro-2-methylphenyl)-3-(4-(methylsulfonyl)phenyl)propanoyl)-1-(2-hydroxyethyl)pyridin-2(1H)-one was reacted with hydroxylamine hydrochloride in the presence of sodium hydrogencarbonate to give the title compound containing less than 10% of the corresponding Z isomer as an off-white solid, MS (ESI+): m/z=489.3 [M+H]+.

Sources & evidence

ORD record
ord-35d1e231e029476da709b5920ca7052f
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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