Hydroxyamine hydrochloride → N-(2-hydroxyethyl)-4-[(3E)-3-hydroxyimino-3-(1-methyl-6-oxo-3-pyridinyl)-1-(2-methylphenyl)propyl]benzamide

HRID 1617708Notes

Reaction equation

[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:31])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH2:13][C:14]([C:16]2[CH:21]=[CH:20][C:19](=[O:22])[N:18]([CH3:23])[CH:17]=2)=O)=[CH:8][CH:7]=1.Cl.[NH2:33][OH:34].C([O-])(O)=O.[Na+]>>[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:31])[C:6]1[CH:7]=[CH:8][C:9]([CH:12]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH2:13]/[C:14](=[N:33]\[OH:34])/[C:16]2[CH:21]=[CH:20][C:19](=[O:22])[N:18]([CH3:23])[CH:17]=2)=[CH:10][CH:11]=1

Participants

Reactant 3

HCID 443297Hydroxyamine hydrochloride

HCID 516892Sodium Bicarbonate

HCID 67015683N-(2-Hydroxy-ethyl)-4-[3-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-1-o-tolyl-propyl]-benzamide

Product 1

HCID 56601931N-(2-hydroxyethyl)-4-[(3E)-3-hydroxyimino-3-(1-methyl-6-oxo-3-pyridinyl)-1-(2-methylphenyl)propyl]benzamide

Procedure

In analogy to example 151, step 3, N-(2-hydroxy-ethyl)-4-[3-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-1-o-tolyl-propyl]-benzamide was reacted with hydroxylamine hydrochloride in the presence of NaHCO3 to give the title compound as a colorless solid, MS (ESI+): m/z=434.4 [M+H]+.

Sources & evidence

ORD record: ord-f14a42b48610419da157a9fd102bd3b1
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765730B2

Reaction notes

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