Acetic Acid → Oxo(phenyl)acetaldehyde methylhydrazone

HRID 1881535Notes

Reaction equation

HRID 1881535 reaction equation
[CH3:1][NH:2][NH2:3].C(O)(=O)C.[C:8]1([C:14]([CH:16]=O)=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O>[CH3:1][NH:2][N:3]=[CH:16][C:14](=[O:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6061MethylhydrazineHCID 14090Phenylglyoxal

Product 1

HCID 67050069Oxo(phenyl)acetaldehyde methylhydrazoneYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixed solution of methylhydrazine (0.554 mL, 10.5 mmol)/acetic acid (1 mL)/water (7.6 mL) was added to phenylglyoxal (1.34 g, 10 mmol) in water (130 mL), and the mixture was stirred at room temperature for 20 hours. The reaction solution was extracted with chloroform, and the extract was dried, filtered, evaporated and dried by means of a vacuum pump to give oxo(phenyl)acetaldehyde methylhydrazone (1.44 g (crude), yield 89%) as a yellow solid.

Workup

  1. extractionThe reaction solution was extracted with chloroform
  2. customthe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. customdried by means of a vacuum pump

Sources & evidence

ORD record
ord-2605aa27782b44aba57074ad48110ae1
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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