3-Phenylprop-2-Enal → HCID 85583141, compound

HRID 359759Notes

Reaction equation

HRID 359759 reaction equation
Cl.[CH3:2][NH:3][OH:4].[CH:5](=O)[CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:15]O>>[CH2:5]([CH:2]=[N+:3]([CH3:15])[O-:4])[CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 3073-Phenylprop-2-EnalHCID 887MethanolHCID 77906N-methylhydroxylamine hydrochloride

Product 1

HCID 85583141HCID 85583141, compoundYield 74%

Procedure

A mixture of 5 g (60 mmole) of methylhydroxylamine hydrochloride and 8 g (61 mmole) of cinnamaldehyde were combined in 25 mL of anhydrous methanol and stirred for 15 minutes at room temperature. The solvent was then removed at reduced pressure and replaced with 50 mL of methylene chloride. The solution was washed with 75 mL of saturated aqueous sodium bicarbonate followed by washing with a brine solution. After drying over anhydrous magnesium sulfate, the solvent was removed under reduced pressure. The solid residue was titurated with ether, filtered and dried. There was obtained 7.2 g (45 mmole or 74% yield) of α-cinnamyl-N-methylnitrone having a melting point of 85-6° C.

Workup

  1. customThe solvent was then removed at reduced pressure
  2. washThe solution was washed with 75 mL of saturated aqueous sodium bicarbonate
  3. washby washing with a brine solution
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-753d8a9e8b62412aaee46daee1467589
Source dataset
uspto-grants-1991_03
Patent number
US05002993

Reaction notes

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