Hydroxyamine hydrochloride → 3-(4-Bromo-phenyl)-1-quinolin-6-yl-3-o-tolyl-propan-1-one oxime

HRID 1617572Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[CH2:9][C:10]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[CH:17][CH:16]=[CH:15]3)=O)=[CH:4][CH:3]=1.Cl.[NH2:30][OH:31].C([O-])(O)=O.[Na+]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[CH2:9][C:10]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[CH:17][CH:16]=[CH:15]3)=[N:30][OH:31])=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 443297Hydroxyamine hydrochloride

HCID 516892Sodium Bicarbonate

HCID 670155803-(4-Bromo-phenyl)-1-quinolin-6-yl-3-o-tolyl-propan-1-one

Product 1

HCID 766713923-(4-Bromo-phenyl)-1-quinolin-6-yl-3-o-tolyl-propan-1-one oxime

Procedure

In analogy to example 74, step 7, from 3-(4-bromo-phenyl)-1-quinolin-6-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 (5.6:1) as a white foam, MS (ESI+): m/z=445.0907 ([M+H]+, 1Br).

Sources & evidence

ORD record: ord-864f6da7cf484e669e7ec7d209853067
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765730B2

Reaction notes

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