Bis(2-hydroxyethyl)(3-methoxy-4-nitrobenzyl)phosphonate → Bis(2-hydroxyethyl)(4-amino-3-methoxybenzyl)phosphonate

HRID 511304Notes

Reaction equation

HRID 511304 reaction equation
[OH:1][CH2:2][CH2:3][O:4][P:5]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[C:14]([O:21][CH3:22])[CH:13]=1)(=[O:10])[O:6][CH2:7][CH2:8][OH:9].[H][H]>CCO.[Pd]>[OH:9][CH2:8][CH2:7][O:6][P:5]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([O:21][CH3:22])[CH:13]=1)(=[O:10])[O:4][CH2:3][CH2:2][OH:1]

Participants

5

Reactant 2

HCID 86654013Bis(2-hydroxyethyl)(3-methoxy-4-nitrobenzyl)phosphonate2×HCID 178418361HCID 178418361, compound

Product 1

HCID 86654012Bis(2-hydroxyethyl)(4-amino-3-methoxybenzyl)phosphonateYield 82.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of bis(2-hydroxyethyl)(3-methoxy-4-nitrobenzyl)phosphonate (Compound 133B, 1.2 g, 3.58 mmol) and 5% Pd/C (0.2 g) in EtOH (80 mL) was hydrogenated under 50 psi hydrogen pressure at 40° C. for 6 h. The reaction mixture was filtered and the filtrate was concentrated to give the desired product (0.9 g, 82%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5715090841f447b8b21939dfe5aa077c
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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