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

HRID 1617790Notes

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][CH:15]=[CH:14][N: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][CH:15]=[CH:14][N:13]=2)=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 443297Hydroxyamine hydrochloride

HCID 516892Sodium Bicarbonate

HCID 67015648(R)-4-(4-Bromophenyl)-1-(pyridin-2-yl)-4-o-tolylbutan-2-one

Product 1

HCID 58043626(NE)-N-[(4R)-4-(4-bromophenyl)-4-(2-methylphenyl)-1-pyridin-2-ylbutan-2-ylidene]hydroxylamine

Procedure

In analogy to example 74, step 7, from (R)-4-(4-bromophenyl)-1-(pyridin-2-yl)-4-o-tolylbutan-2-one and hydroxylamine hydrochloride in the presence of NaHCO3 was prepared the title compound as a colorless oil, MS (ESI+): m/z=409.0904 ([M+H]+, 1Br).

Sources & evidence

ORD record: ord-2c02c6b1167c4b06bdad626cbc0242a3
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765730B2

Reaction notes

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