Malonic Acid → Nitropropanedioic acid

HRID 22467

Reaction equation

HRID 22467 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3]([OH:5])=[O:4].[N+:8]([O-])([O:10]C(=O)C)=[O:9]>C(O)(=O)C.C(OC(=O)C)(=O)C>[N+:8]([CH:2]([C:1]([OH:7])=[O:6])[C:3]([OH:5])=[O:4])([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 867Malonic AcidHCID 11557Acetyl nitrate

Product 1

HCID 19816496Nitropropanedioic acid

Reagents, catalysts & solvents 1

HCID 21895370AcOH AcOAcSolvent

Procedure

Nitration of malonic acid with acetyl nitrate in acetic acid/acetic anhydride was conducted to obtain nitromalonic acid. To the nitromalonic acid is added urea to obtain a condensation reaction mixture which is refluxed to form dilituric acid in situ. Various salts are separately prepared from the dilituric acid in situ using as cation sources potassium chloride, ammonia, and guanidinium chloride. The potassium diliturate salt, ammonium diliturate, guanidinium diliturate salts are each recovered and isolated by filtration.

Sources & evidence

ORD record
ord-1175029bb47c455caecd1dd090779881
Source dataset
uspto-grants-1995_06
Patent number
US05428165

Linked notes

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