Ammonia → Phosphinic acid, (3-aminopropyl)(diethoxymethyl)-, ethyl ester

HRID 2209923Notes

Reaction equation

HRID 2209923 reaction equation
[C:1]([CH2:3][CH2:4][P:5]([CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])(=[O:9])[O:6][CH2:7][CH3:8])#[N:2].N.[H][H]>C(O)C.[Ni]>[NH2:2][CH2:1][CH2:3][CH2:4][P:5]([CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])(=[O:9])[O:6][CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 10037677Ethyl 2-cyanoethyl(diethoxymethyl)phosphinateHCID 178418361HCID 178418361, compound

Product 1

HCID 10422382Phosphinic acid, (3-aminopropyl)(diethoxymethyl)-, ethyl ester

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 9.6 g of ethyl 2-cyanoethyl(diethoxymethyl)phosphinate in 450 ml of ethanol is added to 82 g of an 8% solution of ammonia in ethanol. To this is added 5 ml of Raney Nickel and the resulting mixture is hydrogenated at 1 bar until the theoretical amount of hydrogen has been taken up. The mixture is then filtered, the filtrate is concentrated under reduced pressure and the crude product is distilled to give ethyl 3-aminopropyl(diethoxymethyl)phosphinate, b.p. 150° C./0.01 mbar, 31 p=+46.4 ppm (CDCl3).

Workup

  1. filtrationThe mixture is then filtered
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. distillationthe crude product is distilled

Sources & evidence

ORD record
ord-5b49b1d8f8184912a7103da9638505c3
Source dataset
uspto-grants-1995_10
Patent number
US05457095

Reaction notes

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