Ammonia → Ethyl 3-amino-2-(4-fluorophenyl)propyl(diethoxymethyl)phosphinate

HRID 622902Notes

Reaction equation

HRID 622902 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:22][N+:23]([O-])=O)[CH2:9][P:10]([CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])(=[O:14])[O:11][CH2:12][CH3:13])=[CH:4][CH:3]=1.N.[H][H]>C(O)C.[Ni]>[NH2:23][CH2:22][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[CH2:9][P:10]([CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])(=[O:14])[O:11][CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 14362828Ethyl 2-(4-fluorophenyl)-3-nitropropyl(diethoxymethyl)phosphinateHCID 178418361HCID 178418361, compound

Product 1

HCID 14362834Ethyl 3-amino-2-(4-fluorophenyl)propyl(diethoxymethyl)phosphinate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 5.0 g of ethyl 2-(4-fluorophenyl)-3-nitropropyl(diethoxymethyl)phosphinate in 50 ml of ethanol is added to 40 g of an 8% solution of ammonia in ethanol. To this are added 7 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 and the filtrate is concentrated under reduced pressure to give ethyl 3-amino-2-(4-fluorophenyl)propyl(diethoxymethyl)phosphinate as a viscous oil, 31P=+44.4 ppm (CDCl3).

Workup

  1. filtrationThe mixture is then filtered
  2. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-93a8cf60bc804e8c95f3100e22bb0297
Source dataset
uspto-grants-1988_09
Patent number
US04772738

Reaction notes

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