Ammonia → Isobutyl 3-amino-2-(4-chlorophenyl)-propyl(methyl)phosphinate

HRID 973642Notes

Reaction equation

HRID 973642 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:18][N+:19]([O-])=O)[CH2:9][P:10]([CH3:17])(=[O:16])[O:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:4][CH:3]=1.N.[H][H]>C(O)C.[Ni]>[NH2:19][CH2:18][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:9][P:10]([CH3:17])(=[O:16])[O:11][CH2:12][CH:13]([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 10336939Isobutyl 2-(4-chlorophenyl)-3-nitro-propyl(methyl)phosphinateHCID 178418361HCID 178418361, compound

Product 1

HCID 10335157Isobutyl 3-amino-2-(4-chlorophenyl)-propyl(methyl)phosphinate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 6.8 g of isobutyl 2-(4-chlorophenyl)-3-nitro-propyl(methyl)phosphinate in 80 ml of ethanol is added to 64 g of an 8% solution of ammonia in ethanol. To this are added 8 ml of Raney Nickel slurry and the resulting mixture is hydrogenated at 1 bar until hydrogen treated under reduced pressure to give isobutyl 3-amino-2-(4-chlorophenyl)-propyl(methyl)phosphinate as a viscous oil, 31P N.M.R. spectrum: δ=±54.0 and +53.4 ppm (CDCl3).

Workup

  1. additiontreated under reduced pressure

Sources & evidence

ORD record
ord-24b1aa9b7dfb40b1aadbbc3dc09723de
Source dataset
uspto-grants-1991_11
Patent number
US05064819

Reaction notes

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