HCID 10661075, compound → Diethyl P-[(4-aminophenyl)hydroxymethyl]phosphonate

HRID 350720Notes

Reaction equation

HRID 350720 reaction equation
[OH:1][CH:2]([P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][CH:4]=1>[C].[Pd].CO>[NH2:9][C:6]1[CH:5]=[CH:4][C:3]([CH:2]([P:12](=[O:19])([O:13][CH2:14][CH3:15])[O:16][CH2:17][CH3:18])[OH:1])=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 10661075HCID 10661075, compound

Product 1

HCID 23061737Diethyl P-[(4-aminophenyl)hydroxymethyl]phosphonateYield 80.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a mixed solution of diethyl α-hydroxy-4-nitrobenzylphosphonate (1.42 g) and methanol (30 mL) was added 10% palladium-carbon (0.14 g) and the mixture was stirred at room temperature under an atmospheric hydrogen pressure for 3 hrs. Palladium-carbon was removed from the reaction mixture by filtration and the filtrate was concentrated to give diethyl 4-amino-α-hydroxybenzylphosphonate as a solid (1.02 g, yield 80%).

Workup

  1. customPalladium-carbon was removed from the reaction mixture by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-fac6fbc6f42e4732b1d12a2f954e3d77
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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