Hydroxyamine hydrochloride → Methyl 4-(hydroxyiminomethyl)cinnamate

HRID 583952Notes

Reaction equation

HRID 583952 reaction equation
[CH:1]([C:3]1[CH:14]=[CH:13][C:6]([CH:7]=[CH:8][C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1)=O.Cl.[NH2:16][OH:17].C([O-])(=O)C.[Na+]>CO.O>[OH:17][N:16]=[CH:1][C:3]1[CH:14]=[CH:13][C:6]([CH:7]=[CH:8][C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 53401287Methyl 3-(4-formylphenyl)-2-propenoate

Product 1

HCID 85782432Methyl 4-(hydroxyiminomethyl)cinnamateYield 82.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4.0 g of methyl 4-formylcinnamate are dissolved in 40 ml of methanol, and 1.6 g of hydroxylamine hydrochloride and 1.9 g of sodium acetate are then added successively. The mixture is stirred overnight and then diluted with 300 ml of water, and the resulting precipitate is filtered off with suction. Drying under high vacuum and recrystallization from ethyl acetate/petroleum ether gives 3.56 g of the title compound. The mass spectrum shows the molecular peak MH+ at 206 Da.

Workup

  1. filtrationthe resulting precipitate is filtered off with suction
  2. dry with materialDrying under high vacuum and recrystallization from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-730fd1f3df4d44b3af858824757185ce
Source dataset
uspto-grants-2005_08
Patent number
US06924305B2

Reaction notes

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