Hydrazine hydrate (1:1) → Diethyl (2-cyanoethyl)phosphonate

HRID 424302

Reaction equation

HRID 424302 reaction equation
O.NN.[NH2:4][CH2:5][CH2:6][CH2:7][P:8](=[O:15])([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11]>C(O)C>[C:5]([CH2:6][CH2:7][P:8](=[O:15])([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11])#[N:4]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 78113Diethyl (3-aminopropyl)phosphonate

Product 1

HCID 82369Diethyl (2-cyanoethyl)phosphonateYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of diethyl[3-(N-phthalimido)]propylphosphonate (ex. 5) (3.72 g; 11.4 mmoles), absolute ethanol (46 ml) and hydrazine hydrate (0.78 ml of 98% purity; 15.7 mmoles) is stirred at reflux for 35 min. The mixture is filtered and the solvent is distilled under vacuo. The resulting oil is dissolved in CHCl3 (10 ml) and is filtered again. Solvent removal in vacuo gives a colorless liquid (0.7 g; yield 30%). According to example 4, diethyl 3-aminopropylphosphonate (6) is also obtained from diethyl 2-cyanoethylphosphonate in an analogous fashion followed by vacuum distillation at about 115° C. and 0.18 mbar (yield 80%).

Workup

  1. temperatureat reflux for 35 min
  2. filtrationThe mixture is filtered
  3. distillationthe solvent is distilled under vacuo
  4. dissolutionThe resulting oil is dissolved in CHCl3 (10 ml)
  5. filtrationis filtered again
  6. customSolvent removal in vacuo
  7. customgives a colorless liquid (0.7 g; yield 30%)

Sources & evidence

ORD record
ord-24f0fb6e5da7496fbad561c15f729533
Source dataset
uspto-grants-2012_01
Patent number
US08105689B2

Linked notes

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