Phenylhydrazine → 2-(2-Phenylhydrazono)malonic acid

HRID 1875465

Reaction equation

HRID 1875465 reaction equation
O.[C:2]([O-:9])(=[O:8])[C:3]([C:5]([O-:7])=[O:6])=O.[Na+].[Na+].[C:12]1([NH:18][NH2:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>Cl>[C:12]1([NH:18][N:19]=[C:3]([C:5]([OH:7])=[O:6])[C:2]([OH:9])=[O:8])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 71317420Mesoxalicacidmonohydratedisodiumsalt

Product 1

HCID 5486342-(2-Phenylhydrazono)malonic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Sodium mesoxalate monohydrate (5.00 g, 27.8 mmol) was dissolved in 1 M hydrochloric acid (50 ml) to give a colourless cloudy solution. Phenylhydrazine (3.00 g, 2.72 ml, 27.8 mmol) was added dropwise at room temperature to the stirred mixture. A yellow precipitate formed, was collected by filtration after 90 min and washed with water (50 ml). The filter cake was triturated with ethyl acetate/hexane [1:1], filtered and dried under vacuum. The title compound was isolated as a yellow powder (4.74 g, 22.7 mmol, 82%). LCMS: m/z 207 [M−H]+.

Workup

  1. customto give a colourless cloudy solution
  2. customA yellow precipitate formed
  3. filtrationwas collected by filtration after 90 min
  4. washwashed with water (50 ml)
  5. customThe filter cake was triturated with ethyl acetate/hexane [1:1]
  6. filtrationfiltered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-4ebe665daa844f118a65bb9244cb9d08
Source dataset
uspto-grants-2012_11
Patent number
US08309552B2

Linked notes

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