4-(Benzylamino)-3,5-difluoro-2,6-dimethoxybenzoic acid → N-benzyl-2,6-difluoro-3,5-dimethoxyaniline

HRID 459941Notes

Reaction equation

HRID 459941 reaction equation
[CH2:1]([NH:8][C:9]1[C:17]([F:18])=[C:16]([O:19][CH3:20])[C:12](C(O)=O)=[C:11]([O:21][CH3:22])[C:10]=1[F:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClC1C=CC=CC=1>[CH2:1]([NH:8][C:9]1[C:10]([F:23])=[C:11]([O:21][CH3:22])[CH:12]=[C:16]([O:19][CH3:20])[C:17]=1[F:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 184448114-(Benzylamino)-3,5-difluoro-2,6-dimethoxybenzoic acid

Product 1

HCID 18444842N-benzyl-2,6-difluoro-3,5-dimethoxyanilineYield 94.3%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

4-(Benzylamino)-3,5-difluoro-2,6-dimethoxybenzoic acid (9.1 g, 28.1 mmol) was treated with chlorobenzene (45 mL) and the solution heated to reflux under nitrogen where it was maintained for 16 hours. The solution was cooled to room temperature and extracted with saturated, aqueous sodium bicarbonate solution (2×5 mL) followed by water. The organic layer was concentrated under reduced pressure to an oil that crystallized on standing. This was recrystallized from heptane (10 mL) and toluene (5 mL), the mixture cooled to −10° C., filtered and the crystals washed with heptane (10 mL) and vacuum dried at 35° C. to give N-benzyl-2,6-difluoro-3,5-dimethoxyaniline (7.4 g, 26.5 mmol). mp: 65° C.–66° C.

Workup

  1. temperaturethe solution heated
  2. temperatureto reflux under nitrogen where it
  3. temperaturewas maintained for 16 hours
  4. extractionextracted with saturated, aqueous sodium bicarbonate solution (2×5 mL)
  5. concentrationThe organic layer was concentrated under reduced pressure to an oil that
  6. customcrystallized
  7. customThis was recrystallized from heptane (10 mL) and toluene (5 mL)
  8. temperaturethe mixture cooled to −10° C.
  9. filtrationfiltered
  10. washthe crystals washed with heptane (10 mL) and vacuum
  11. customdried at 35° C.

Sources & evidence

ORD record
ord-d25f3cf99e8344a4945661a87829c6a5
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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