Hydroxyamine hydrochloride → (NZ)-N-[(4R)-4-(4-bromophenyl)-4-(2-methylphenyl)-1-pyridin-4-ylbutan-2-ylidene]hydroxylamine

HRID 1617835Notes

Reaction equation

[Br: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](=O)[CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.Cl.[NH2:27][OH:28].C(=O)([O-])O.[Na+]>>[Br: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](=[N:27]/[OH:28])/[CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 443297Hydroxyamine hydrochloride

HCID 516892Sodium Bicarbonate

HCID 66666163(R)-4-(4-bromophenyl)-1-(pyridin-4-yl)-4-o-tolylbutan-2-one

Product 1

HCID 58043446(NZ)-N-[(4R)-4-(4-bromophenyl)-4-(2-methylphenyl)-1-pyridin-4-ylbutan-2-ylidene]hydroxylamine

Procedure

In analogy to example 1, step 2, from (R)-4-(4-bromo-phenyl)-1-pyridin-4-yl-4-o-tolyl-butan-2-one and hydroxylamine hydrochloride in the presence of sodium hydrogencarbonate was prepared the title compound as a colourless oil, MS (ESI+): m/z=409.1 ([M+H]+, 1Br).

Sources & evidence

ORD record: ord-3867f275f74b4efaabbbad23800a28b2
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765730B2

Reaction notes

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