N-benzyl-2,6-difluoro-3,5-dimethoxyaniline → 2,6-Difluoro-3,5-dimethoxybenzenamine

HRID 459942Notes

Reaction equation

HRID 459942 reaction equation
C([NH:8][C:9]1[C:14]([F:15])=[C:13]([O:16][CH3:17])[CH:12]=[C:11]([O:18][CH3:19])[C:10]=1[F:20])C1C=CC=CC=1.[H][H]>C1COCC1.[OH-].[OH-].[Pd+2]>[F:15][C:14]1[C:13]([O:16][CH3:17])=[CH:12][C:11]([O:18][CH3:19])=[C:10]([F:20])[C:9]=1[NH2:8]

Participants

5

Reactant 2

HCID 18444842N-benzyl-2,6-difluoro-3,5-dimethoxyanilineHCID 178418361HCID 178418361, compound

Product 1

HCID 102618922,6-Difluoro-3,5-dimethoxybenzenamineYield 94.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

N-Benzyl-2,6-difluoro-3,5-dimethoxyaniline (6.0 g, 21.5 mmol) was dissolved in THF (40 mL) and the solution hydrogenated over 20% palladium hydroxide on carbon catalyst (0.6 g) at 20° C.–25° C. 48–50 psi hydrogen pressure for 16 hours. The mixture was filtered, the catalyst washed with THF (2×15 mL) and the combined filtrates concentrated to a solid. This was recrystallized from heptane (10 mL) and toluene (4.5 mL). The mixture was cooled to −10° C. before filtering. The crystals were washed with heptane (2×10 ML) and vacuum dried at 35° C. to give 2,6-difluoro-3,5-dimethoxyaniline as off-white needles (3.85 g, 20.4 mmol). mp: 78° C.–79° C.

Workup

  1. filtrationThe mixture was filtered
  2. washthe catalyst washed with THF (2×15 mL)
  3. concentrationthe combined filtrates concentrated to a solid
  4. customThis was recrystallized from heptane (10 mL) and toluene (4.5 mL)
  5. filtrationbefore filtering
  6. washThe crystals were washed with heptane (2×10 ML) and vacuum
  7. customdried at 35° C.

Sources & evidence

ORD record
ord-43d6a613664e4a7a8ad29206dab72fc8
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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