Acetic Acid → 2-Oxopropanal (3-methoxyphenyl)hydrazone

HRID 1880332Notes

Reaction equation

HRID 1880332 reaction equation
C(O)(=O)C.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([NH:13][NH2:14])[CH:10]=[CH:11][CH:12]=1.[CH:15](=O)[C:16]([CH3:18])=[O:17]>O>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([NH:13][N:14]=[CH:15][C:16](=[O:17])[CH3:18])[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 880MethylglyoxalHCID 423605(3-Methoxyphenyl)hydrazine

Product 1

HCID 669204522-Oxopropanal (3-methoxyphenyl)hydrazoneYield 33.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Acetic acid (1.7 mL) was added to a solution of 3-methoxyphenylhydrazine (3.0 g, 17 mmol) in water (35 mL). This mixture was then added dropwise to a solution of pyruvaldehyde (3.1 g, 2.8 mL, 17 mmol) in water (45 ml) over 15 minutes. The mixture was stirred for two days and solids were removed by filtration and washed with water to obtain 2-oxopropanal (3-methoxyphenyl)hydrazone as a black solid (1.1 g, 33%).

Workup

  1. customsolids were removed by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-27661ca9fd9e4cbd901258b073d45260
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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