Acetone → Benzenamine, 4-fluoro-N-(1-methylethyl)-

HRID 52796Notes

Reaction equation

HRID 52796 reaction equation
[C:1]1(C)[CH:6]=CC=C[CH:2]=1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1.CC(C)=O>[Pt].O>[F:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH:1]([CH3:6])[CH3:2])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 1140TolueneHCID 9590p-Fluoronitrobenzene

Product 1

HCID 154403Benzenamine, 4-fluoro-N-(1-methylethyl)-

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 962WaterSolvent2×

Conditions

Temperature
42.5 °C

Procedure

520 parts of toluene, 423 parts (3 mol) of 4-fluoronitrobenzene, 192 parts (3.3 mol) of acetone and 8 parts of catalyst (5% Pt on charcoal, water-moist, water content 50%) are placed in a hydrogenation autoclave. After the gas space has been flushed three times with each of nitrogen and hydrogen, the mixture is heated to from 80°=0 to 85° C. with stirring and reduced at a hydrogen pressure of from 0.2 to 1.0 MPa. When after about 2 hours the uptake of hydrogen falls sharply, the pressure is raised to 2.0 MPa and stirring is continued at 85° C for 30 minutes until there is no longer any drop in pressure. The batch is cooled to 60° C., the autoclave is let down and flushed with nitrogen, and the catalyst is filtered off on a pressure filter at from 50° to 60° C. The aqueous phase is separated off from the filtrate and toluene is distilled off until the water content of the solution is <0.02%. The solution is processed further in accordance with Example 2.

Workup

  1. customAfter the gas space has been flushed three times with each of nitrogen and hydrogen
  2. temperaturethe pressure is raised to 2.0 MPa
  3. stirringstirring
  4. waitis continued at 85° C for 30 minutes until there
  5. temperatureThe batch is cooled to 60° C.
  6. customflushed with nitrogen
  7. filtrationthe catalyst is filtered off on a pressure
  8. filtrationfilter at from 50° to 60° C
  9. customThe aqueous phase is separated off from the filtrate and toluene
  10. distillationis distilled off until the water content of the solution

Sources & evidence

ORD record
ord-0173e26d921d41c69b96b6802eb121c1
Source dataset
uspto-grants-1997_04
Patent number
US05616799

Reaction notes

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