Bis(2-methoxyethyl)(4-nitro-3-methoxybenzyl)phosphonate → Bis(2-methoxyethyl)(4-amino-3-methoxybenzyl)phosphonate

HRID 511459Notes

Reaction equation

HRID 511459 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][P:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16]([O:23][CH3:24])[CH:15]=1)(=[O:12])[O:7][CH2:8][CH2:9][O:10][CH3:11].[H][H]>CO.[Pd]>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][P:6](=[O:12])([O:7][CH2:8][CH2:9][O:10][CH3:11])[O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:15][C:16]=1[O:23][CH3:24]

Participants

5

Reactant 2

HCID 86654043Bis(2-methoxyethyl)(4-nitro-3-methoxybenzyl)phosphonate2×HCID 178418361HCID 178418361, compound

Product 1

HCID 86654042Bis(2-methoxyethyl)(4-amino-3-methoxybenzyl)phosphonateYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of bis(2-methoxyethyl)(4-nitro-3-methoxybenzyl)phosphonate (Compound 217D, 4.5 g, 12.4 mmol) and 5% Pd/C (2 g, wet) in MeOH (100 mL) was hydrogenated under 50 psi hydrogen pressure at 50° C. for 18 h. The reaction mixture was filtered and the filtrate was concentrated to give the desired product (4 g, 97%). 1H NMR (DMSO-d6, 400 MHz): δ=3.11 (d, J=21.2 Hz, 2 H), 3.34 (s, 6 H), 3.49 (m, 4 H), 3.81 (s, 3 H), 4.05 (m, 4 H), 6.12 (d, J=8.4 Hz, 2 H), 6.20 (dd, J=8.4 Hz, 1 H), 6.78 (s, 1 H).

Workup

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

Sources & evidence

ORD record
ord-07ba2a3f6fe9413f88f666104bc0ca24
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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