Methylglyoxal → 2-Oxopropanal benzylhydrazone

HRID 1880337Notes

Reaction equation

HRID 1880337 reaction equation
Cl.[CH2:2]([NH:9][NH2:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:11](=O)[C:12]([CH3:14])=[O:13]>O.C(Cl)Cl>[CH2:2]([NH:9][N:10]=[CH:11][C:12](=[O:13])[CH3:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 880MethylglyoxalHCID 14084Hydrazine, (phenylmethyl)-, hydrochloride (1:1)

Product 1

HCID 669205262-Oxopropanal benzylhydrazoneYield 100.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzylhydrazine hydrochloride (11.1 g, 57.1 mmol) in water (100 mL) was added dropwise a solution of pyruvaldehyde (10.3 g, 9.3 mL, 57.1 mmol) in water (500 mL). The mixture was stirred at room temperature overnight. The reaction mixture was diluted with CH2Cl2 (4×150 mL). The combined organic extracts were washed with saturated aqueous NaCl, dried over Na2SO4, filtered and concentrated to provide 2-oxopropanal benzylhydrazone (10.1 g, 100%).

Workup

  1. washThe combined organic extracts were washed with saturated aqueous NaCl
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-26d515651dec4e98aecf87aed046bbe2
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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