Hydrochloric Acid → 4,5-Difluoro-2-nitroaniline

HRID 1414080Notes

Reaction equation

HRID 1414080 reaction equation
CC([NH:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([F:14])=[C:7]([F:15])[CH:6]=1)=O.Cl>>[F:14][C:8]1[C:7]([F:15])=[CH:6][C:5]([NH2:4])=[C:10]([N+:11]([O-:13])=[O:12])[CH:9]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 540127N-(4,5-Difluoro-2-nitrophenyl)acetamide

Product 1

HCID 1571514,5-Difluoro-2-nitroaniline

Procedure

A mixture of 6.51 g. of 4,5-difluoro-2-nitroacetanilide and 100 ml. of 6 N aqueous hydrochloric acid was heated to refluxing temperature for about 2 hours. The reaction mixture was then cooled. Crystals which formed were separated by filtration, and the separated crystals were washed with water, dried, and recrystallized from a hexane-dichloromethane solvent mixture. A yield of 5.0 g. of 4,5-difluoro-2-nitroaniline was obtained, melting at 106°-108° C.

Workup

  1. additionA mixture of 6.51 g
  2. temperatureto refluxing temperature for about 2 hours
  3. temperatureThe reaction mixture was then cooled
  4. customCrystals which formed
  5. customwere separated by filtration
  6. washthe separated crystals were washed with water
  7. customdried
  8. customrecrystallized from a hexane-dichloromethane solvent mixture

Sources & evidence

ORD record
ord-d1f7c6865dd34561b0eacffab8572b6f
Source dataset
uspto-grants-1981_02
Patent number
US04252954

Reaction notes

Loading…