Hydroxyamine hydrochloride → 3-(4-Bromo-phenyl)-1-(2-fluoro-6-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one oxime

HRID 1617574Notes

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:17]=[C:16]([CH3:18])[N:15]=[C:14]([F:19])[CH:13]=2)=O)=[CH:4][CH:3]=1.Cl.[NH2:28][OH:29].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:17]=[C:16]([CH3:18])[N:15]=[C:14]([F:19])[CH:13]=2)=[N:28][OH:29])=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 443297Hydroxyamine hydrochloride

HCID 516892Sodium Bicarbonate

HCID 670155133-(4-Bromo-phenyl)-1-(2-fluoro-6-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one

Product 1

HCID 1363600133-(4-Bromo-phenyl)-1-(2-fluoro-6-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one oxime

Procedure

In analogy to example 74, step 7, from 3-(4-bromo-phenyl)-1-(2-fluoro-6-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 (2.4:1) as a colorless oil, MS (ESI+): m/z=427.0804 ([M+H]+, 1Br).

Sources & evidence

ORD record: ord-5ebb52e79fe448f294cf1a4fb0b32b9e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765730B2

Reaction notes

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