N-(2-fluoro-4-nitrophenyl)acetamide → n-(4-Amino-2-fluorophenyl)acetamide

HRID 373442Notes

Reaction equation

HRID 373442 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[F:14])(=[O:3])[CH3:2]>[Pd].CO>[NH2:11][C:8]1[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[C:6]([F:14])[CH:7]=1

Participants

4

Reactant 1

HCID 3412310N-(2-fluoro-4-nitrophenyl)acetamide

Product 1

HCID 255648n-(4-Amino-2-fluorophenyl)acetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

198 g (1 mol) of 1-acetylamino-2-fluoro-4-nitrobenzene are transferred into a stainless steel autoclave together with 510 ml of methanol, about 3 g of palladium-on-charcoal (5%) are added and catalytic reduction is carried out in the course of 4 hours at 50° C. under a hydrogen pressure of 15 bar. After the catalyst has been removed, 450 ml of methanol are distilled off from the reaction solution in vacuo, the product which has precipitated is filtered off with suction and the residue is washed with a little methanol and dried at 50°-60° C. in a vacuum cabinet.

Workup

  1. additionare added
  2. customis carried out in the course of 4 hours at 50° C. under a hydrogen
  3. customAfter the catalyst has been removed
  4. distillation450 ml of methanol are distilled off from the reaction solution in vacuo
  5. customthe product which has precipitated
  6. filtrationis filtered off with suction
  7. washthe residue is washed with a little methanol
  8. customdried at 50°-60° C. in a vacuum cabinet

Sources & evidence

ORD record
ord-d99fe9a7fe2043418c24bdf86339d290
Source dataset
uspto-grants-1992_11
Patent number
US05163970

Reaction notes

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