Diisopropylethylamine → (NZ)-N-[2-(4-bromo-2-pyridinyl)-1-(4-methoxyphenyl)ethylidene]hydroxylamine

HRID 1475929Notes

Reaction equation

HRID 1475929 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=O)[CH:3]=1.C(N(CC)C(C)C)(C)C.Cl.[NH2:29][OH:30]>CO>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8]/[C:9](/[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[N:29]/[OH:30])[CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 682760292-(4-Bromopyridin-2-yl)-1-(4-methoxyphenyl)ethanone

Product 1

HCID 140634899(NZ)-N-[2-(4-bromo-2-pyridinyl)-1-(4-methoxyphenyl)ethylidene]hydroxylamineYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 2-(4-bromopyridin-2-yl)-1-(4-methoxyphenyl)ethanone (3.8 g, 12.4 mmol) and N,N-diisopropylethylamine (5.4 mL, 31 mmol) in methanol (60 mL) at room temperature was added hydroxylamine hydrochloride (1.7 g, 24.8 mmol). The mixture was stirred at 60° C. for 2 days. After cooling to room temperature, the precipitate formed was filtered and dried under vacuum to afford white needles (2.7 g, 68%). The material was used as is in the next step. LCMS m/z 321.0; 323.0 (M+H)+, ret. time=2.37 min.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe precipitate formed
  3. filtrationwas filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-da34e97b64c74a9883dc95975a5591b8
Source dataset
uspto-grants-2015_04
Patent number
US09018395B2

Reaction notes

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