Hydroxyamine hydrochloride → 3-(4'-Methane sulfonyl-biphenyl-3-yl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one oxime

HRID 1617544Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])[CH2:18][C:19]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([CH3:27])[CH:22]=3)=O)[CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Cl.[NH2:36][OH:37].C([O-])(O)=O.[Na+]>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])[CH2:18][C:19]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([CH3:27])[CH:22]=3)=[N:36][OH:37])[CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

Reactant 3

HCID 443297Hydroxyamine hydrochloride

HCID 516892Sodium Bicarbonate

HCID 670155223-(4'-Methanesulfonyl-biphenyl-3-yl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one

Product 1

HCID 1363479413-(4'-Methane sulfonyl-biphenyl-3-yl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one oxime

Procedure

In analogy to example 74, step 7, 3-(4′-methanesulfonyl-biphenyl-3-yl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one and hydroxylamine hydrochloride in the presence of NaHCO3 was prepared the title compound as a mixture of E and Z isomers (4.8:1) as a white foam, MS (ESI+): m/z=485.19 ([M+H]+).

Sources & evidence

ORD record: ord-9f93cea4eda549c9a573455e65953fb0
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765730B2

Reaction notes

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