Phenylhydrazine → 2-(2-Phenylhydrazono)malonic acid

HRID 1599074Notes

Reaction equation

HRID 1599074 reaction equation
O.O=[C:3]([C:7]([OH:9])=[O:8])[C:4]([OH:6])=[O:5].[C:10]1([NH:16][NH2:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)C.O>[C:10]1([NH:16][N:17]=[C:3]([C:7]([OH:9])=[O:8])[C:4]([OH:6])=[O:5])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 7516PhenylhydrazineHCID 20057180Ketomalonic acid hydrate

Product 1

HCID 5486342-(2-Phenylhydrazono)malonic acidYield 94.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a vigorously stirred solution of ketomalonic acid monohydrate (29.33 g) in ethanol (140 mL) and water (300 mL) at ambient temperature was added phenylhydrazine (23.3 g) dropwise over a 40 minute period. The resultant slurry was stirred overnight at ambient temperature. The solid was separated by filtration, washed sucessively with cold water (100 mL) and ethanol (25 mL) and air dried. Subsequent drying was performed at 75° C. overnight in a vacuum oven to give the title compound as a yellow solid (42.38 g). 1H (300 MHz, DMSO-d6): d 7.12(t, 1H), 7.35-7.48(m, 4H); m.p.: 155°-157° C. (dec).

Workup

  1. customThe solid was separated by filtration
  2. washwashed sucessively with cold water (100 mL) and ethanol (25 mL) and air
  3. customdried
  4. customSubsequent drying
  5. waitwas performed at 75° C. overnight in a vacuum oven

Sources & evidence

ORD record
ord-2a14a011d82f4ddfa293dd5c8d2df1de
Source dataset
uspto-grants-1998_04
Patent number
US05739129

Reaction notes

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