Ammonia → 2-Chloro-4-trifluoromethylaniline

HRID 1892545Notes

Reaction equation

HRID 1892545 reaction equation
[F-].[K+].[Cl:3][C:4]1[CH:5]=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:8][C:9]=1[Cl:10].[NH3:15]>CN1CCCC1=O>[Cl:3][C:4]1[CH:5]=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:8][C:9]=1[NH2:15].[Cl:10][C:9]1[CH:8]=[CH:7][C:6]([C:11]([F:14])([F:13])[F:12])=[CH:5][C:4]=1[NH2:15]

Participants

6

Reactant 3

HCID 222Ammonia3×HCID 94813,4-DichlorobenzotrifluorideHCID 522689Potassium Fluoride

Product 2

HCID 8475Benzenamine, 2-chloro-5-(trifluoromethyl)-Yield 13%HCID 1620012-Chloro-4-trifluoromethylanilineYield 77%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
247.5 °C

Procedure

N-methylpyrrolidone (1050 ml) was charged in an autoclave along with 102 g anhydrous activated potassium fluoride, 377 g 3,4-dichlorobenzotrifluoride was added. Ammonia (158 g) gas was passed in the reactor from the pressure pot at ambient temperature. The content of the reactor was heated to 245° C.-250° C. over a period of 2 hours to get reactor pressure of 30-32 kg/cm2. Excess NH3 was fed from the pressure pot to maintain the reactor pressure at 38-40 kg/cm2 at 245-250° C. liquid temperature. Reaction mixture was maintained at 245-250° C. and at 38-40 kg/cm2 pressure for further 8 hours. Reaction mixture was cooled to ambient temperature and NH3 was vented and recovered. Reaction mixture was filtered and on fractionation gave 77% yield of 2-chloro-4-trifluoromethylaniline and 13% yield of 2-chloro-5-trifluoromethyl aniline based on consumed 3,4-dichlorobenzotrifluoride.

Workup

  1. additionwas added
  2. customwas passed in the reactor from the pressure pot at ambient temperature
  3. temperatureThe content of the reactor was heated to 245° C.-250° C. over a period of 2 hours
  4. customto get reactor pressure of 30-32 kg/cm2
  5. customReaction mixture
  6. temperaturewas maintained at 245-250° C. and at 38-40 kg/cm2 pressure for further 8 hours
  7. customReaction mixture
  8. temperaturewas cooled to ambient temperature
  9. customrecovered
  10. customReaction mixture
  11. filtrationwas filtered and on fractionation

Sources & evidence

ORD record
ord-147e19f9713746b6825688bb03be1c9b
Source dataset
uspto-grants-2013_08
Patent number
US08507693B2

Reaction notes

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