(3-Methoxy-4-nitrophenyl)(dimethyl)phosphane oxide → (4-Amino-3-methoxyphenyl)dimethylphosphine oxide

HRID 1472046Notes

Reaction equation

HRID 1472046 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([P:12](=[O:15])([CH3:14])[CH3:13])[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>CCO.[Pd]>[CH3:14][P:12]([C:5]1[CH:6]=[CH:7][C:8]([NH2:9])=[C:3]([O:2][CH3:1])[CH:4]=1)([CH3:13])=[O:15]

Participants

4

Reactant 1

HCID 67052712(3-Methoxy-4-nitrophenyl)(dimethyl)phosphane oxide

Product 1

HCID 67052699(4-Amino-3-methoxyphenyl)dimethylphosphine oxideYield 100.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (3-methoxy-4-nitrophenyl)(dimethyl)phosphane oxide (0.1 g, 0.44 mmol) in 5 mL of EtOH was added 10% weight of palladium on carbon (0.2 g). The mixture was purged with argon, and hydrogenated under 30 psi for 2 h. The mixture was passed through Celite to a flask containing HCl in ethanol. Concentration of the filtrate gave the final product (0.088 g, 86% yield). MS/ES+: m/z=199.

Workup

  1. customThe mixture was purged with argon
  2. customThe mixture was passed through Celite to a flask
  3. additioncontaining HCl in ethanol

Sources & evidence

ORD record
ord-fc94d3219988474396a443ed189f0cf9
Source dataset
uspto-grants-2015_04
Patent number
US09012462B2

Reaction notes

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