Hydroxyamine hydrochloride → 5-[(E)-C-[2-(4-bromo-2-fluorophenyl)-2-(2-methylphenyl)ethyl]-N-hydroxycarbonimidoyl]-1-methylpyridin-2-one

HRID 1617687Notes

Reaction equation

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

Participants

Reactant 3

HCID 443297Hydroxyamine hydrochloride

HCID 516892Sodium Bicarbonate

HCID 666692875-[3-(4-Bromo-2-fluoro-phenyl)-3-o-tolyl-propionyl]-1-methyl-1H-pyridin-2-one

Product 1

HCID 580432005-[(E)-C-[2-(4-bromo-2-fluorophenyl)-2-(2-methylphenyl)ethyl]-N-hydroxycarbonimidoyl]-1-methylpyridin-2-one

Procedure

In analogy to example 151, step 3, 5-[3-(4-bromo-2-fluoro-phenyl)-3-o-tolyl-propionyl]-1-methyl-1H-pyridin-2-one was reacted with hydroxylamine hydrochloride in the presence of NaHCO3 to give the title compound as a colorless solid, MS (ESI+): m/z=443.1 [M+H]+.

Sources & evidence

ORD record: ord-0c7b6981c2174dd9bd09ed53daeb9135
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765730B2

Reaction notes

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