Hydroxyamine hydrochloride → N-hydroxy-3-(3-methylphenyl)prop-2-yn-1-imine

HRID 2254448Notes

Reaction equation

HRID 2254448 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][CH:10]=O)[CH:5]=[CH:6][CH:7]=1.Cl.[NH2:13][OH:14].CCCCCC.C(OCC)(=O)C>C(O)C>[CH3:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][CH:10]=[N:13][OH:14])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 107731013-(m-Tolyl)propiolaldehydeHCID 21226206Ethyl acetate hexane

Product 1

HCID 86662876N-hydroxy-3-(3-methylphenyl)prop-2-yn-1-imineYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

130 mg of the resulting aldehyde was dissolved in 20 ml of ethanol, and 5 ml of an aqueous solution of 70 mg of hydroxylamine hydrochloride was added. The solvent was evaporated under reduced pressure. The residue was purified by medium-pressure liquid chromatography column: Lobar column, size A, Lichroprep Si 60 (E. Merck Co.); eluting solvent: hexane/ethyl acetate=-10/1] to give 122 mg (yield 85%) of 3-(3-methylphenyl)-2-propynaldehyde oxime as a pale yellow oil.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThe residue was purified by medium-pressure liquid chromatography column

Sources & evidence

ORD record
ord-321cb3613a6f4f7fb291ec95c3863002
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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