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

HRID 1165343Notes

Reaction equation

HRID 1165343 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH2:23][N+:24]([O-])=O)[CH2:10][P:11]([CH:16]([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])(=[O:15])[O:12][CH2:13][CH3:14])=[CH:5][CH:4]=1.N.[H][H]>C(O)C.[Ni]>[NH2:24][CH2:23][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[CH2:10][P:11]([CH:16]([O:17][CH2:18][CH3:19])[O:20][CH2:21][CH3:22])(=[O:15])[O:12][CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 14362830Ethyl 2-(4-methoxyphenyl)-3-nitropropyl(diethoxymethyl)phosphinateHCID 178418361HCID 178418361, compound

Product 1

HCID 14362836Ethyl 3-amino-2-(4-methoxyphenyl)propyl(diethoxymethyl)phosphinate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 6.6 g of ethyl 2-(4-methoxyphenyl)-3-nitropropyl(diethoxymethyl)phosphinate in 50 ml of ethanol is added to 52 g of an 8% solution of ammonia in ethanol. To this are added 8 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-methoxyphenyl)propyl(diethoxymethyl)phosphinate as a viscous oil, 31P=+44.5 ppm (CDCl3).

Workup

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

Sources & evidence

ORD record
ord-6ff35bcfd7d0466c8e97d61f40eca726
Source dataset
uspto-grants-1990_03
Patent number
US04908465

Reaction notes

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