Cyanoacetic acid → 3-Amino-3,3-diphosphonopropanoic acid

HRID 866538Notes

Reaction equation

HRID 866538 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=[O:5])#[N:2].[P:7]([OH:10])([OH:9])[OH:8]>CC(C)=O>[NH2:2][C:1]([P:7]([OH:10])([OH:9])=[O:8])([P:7]([OH:10])([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 9740Cyanoacetic acidHCID 107909Phosphorous acid

Product 1

HCID 205565153-Amino-3,3-diphosphonopropanoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
165 °C

Procedure

A mixture of cyanoacetic acid (4.3 g, 0.5 mole), phosphorous acid (8.2 g, 0.1 mole), ISOPAR-M (20 g), and the wetting agents (0.25 g each) was heated at 165° C for 2 hours. The product was worked up with acetone to get yellow crystals of 1-amino-1,1-diphosphono-2-carboxy ethane, m.p. 255° C (decomposition), 55%, associated with traces of impurities.

Sources & evidence

ORD record
ord-c6f4be4f1c3b4c00887c53a220298922
Source dataset
uspto-grants-1978_07
Patent number
US04100167

Reaction notes

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