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

HRID 542326Notes

Reaction equation

HRID 542326 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH2:21][N+:22]([O-])=O)[CH2:10][P:11]([CH:14]([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])(=[O:13])[O-:12])=[CH:5][CH:4]=1.N.[H][H].[CH2:28](O)[CH3:29]>[Ni]>[NH2:22][CH2:21][CH:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH2:10][P:11]([CH:14]([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])(=[O:13])[O:12][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 702Ethanol2×HCID 20209951HCID 20209951, compoundHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

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-8d0f95f11bb64ff48d0953a8a4c98153
Source dataset
uspto-grants-1987_04
Patent number
US04656298

Reaction notes

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