Acetaldehyde, 2,2-dimethoxy- → N-(2,2-dimethoxyethyl)-4-fluoro-3-methoxyaniline

HRID 23947

Reaction equation

HRID 23947 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[O:9][CH3:10].[CH3:11][O:12][CH:13]([O:16][CH3:17])[CH:14]=O>C(O)C.[Pd]>[CH3:11][O:12][CH:13]([O:16][CH3:17])[CH2:14][NH:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[C:3]([O:9][CH3:10])[CH:4]=1

Participants

5

Reactant 2

HCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 27745334-Fluoro-3-methoxyaniline

Product 1

HCID 22570019N-(2,2-dimethoxyethyl)-4-fluoro-3-methoxyanilineYield 101.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-fluoro-3-methoxyaniline (0.98 g 6.9 mmol) in ethanol (20 ml) was added glyoxal 1,1-dimethyl acetal (0.89 g 8.27 mmol). Pd/C 5% (50 mg) was added and the mixture hydrogenated. Removal of the catalyst by filtration and evaporation of solvent in vacuo gave N-(2,2-dimethoxyethyl)-4-fluoro-3-methoxyaniline 1.6 g

Workup

  1. customRemoval of the catalyst
  2. filtrationby filtration and evaporation of solvent in vacuo

Sources & evidence

ORD record
ord-a5bf9884b51f40babe1c53423ffc7dc7
Source dataset
uspto-grants-2005_02
Patent number
US06855715B1

Linked notes

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