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

HRID 1617671Notes

Reaction equation

HRID 1617671 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:22])[N:16]([CH2:18][CH2:19][O:20][CH3:21])[CH:17]=2)=O)=[CH:4][CH:3]=1.Cl.[NH2:31][OH:32].C([O-])(O)=O.[Na+]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[CH2:9]/[C:10](/[C:12]2[CH:13]=[CH:14][C:15](=[O:22])[N:16]([CH2:18][CH2:19][O:20][CH3:21])[CH:17]=2)=[N:31]\[OH:32])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 670155825-[3-(4-Bromo-phenyl)-3-o-tolyl-propionyl]-1-(2-methoxy-ethyl)-1H-pyridin-2-one

Product 1

HCID 580433425-[(E)-C-[2-(4-bromophenyl)-2-(2-methylphenyl)ethyl]-N-hydroxycarbonimidoyl]-1-(2-methoxyethyl)pyridin-2-one

Procedure

In analogy to example 151, step 3, 5-[3-(4-bromo-phenyl)-3-o-tolyl-propionyl]-1-(2-methoxy-ethyl)-1H-pyridin-2-one was reacted with hydroxylamine hydrochloride in the presence of NaHCO3 to give the title compound as a colorless amorphous solid, MS (ESI+): m/z=469.2 [M+H]+.

Sources & evidence

ORD record
ord-999f1a3a5fe042df86c3fbb70929f78b
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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