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

HRID 1947791Notes

Reaction equation

HRID 1947791 reaction equation
[CH2:1]([O:3][P:4]([C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[H][H]>[Pd].CCO>[CH2:6]([O:5][P:4]([C:9]1[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=1)(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

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-16ea482e2ed340a49c5d4fdfee0f3533
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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