Phenylhydrazine → 2-(2-Phenylhydrazono)malonic acid

HRID 1416107Notes

Reaction equation

HRID 1416107 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-f5a07a0fb14e4af69cbcf50d1e4bc63c
Source dataset
uspto-grants-1999_06
Patent number
US05910495

Reaction notes

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