Diethyl(4-nitrophenyl)phosphonate → Diethyl (4-aminophenyl)phosphonate

HRID 511218Notes

Reaction equation

HRID 511218 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].CCO>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([P:10](=[O:17])([O:11][CH2:12][CH3:13])[O:14][CH2:15][CH3:16])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 284865Diethyl(4-nitrophenyl)phosphonateHCID 178418361HCID 178418361, compound

Product 1

HCID 273213Diethyl (4-aminophenyl)phosphonateYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of diethyl (4-nitrophenyl)phosphonate (150 mg, 0.58 mmol), EtOH (40 ml) and 10% Pd/C (30 mg) was hydrogenated under 50 psi of hydrogen pressure at 40° C. for 6 h. After cooling to room temperature, the reaction mixture was filtered and the filtrate concentrated in vacuo to afford 130 mg of desired diethyl (4-aminophenyl)phosphonate (yield: 98%), which was used directly in further chemistries without purification.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-f842427ccf7c41a7a71ee9cfbcc452a0
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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