Hydroxyamine hydrochloride → (R)-3-(4-Hydroxy-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one oxime

HRID 1617967Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[CH:13]=2)=O)=[CH:4][CH:3]=1.Cl.[NH2:27][OH:28].C(=O)([O-])O.[Na+]>>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[CH:13]=2)=[N:27][OH:28])=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 443297Hydroxyamine hydrochloride

HCID 516892Sodium Bicarbonate

HCID 67015734(R)-3-(4-Hydroxy-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one

Product 1

HCID 136360063(R)-3-(4-Hydroxy-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one oxime

Procedure

In analogy to example 132, step 6, from (R)-3-(4-hydroxy-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one and hydroxylamine hydrochloride in the presence of sodium hydrogencarbonate was prepared the title compound as a white solid, MS (ESI+): m/z=347.2 ([M+H]+).

Sources & evidence

ORD record: ord-92c5f6ab289449e3a8e887eff558dc54
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765730B2

Reaction notes

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