4-Chloro-3,5-dinitrobenzotrifluoride → 5-(Trifluoromethyl)benzene-1,3-diamine

HRID 1742116Notes

Reaction equation

HRID 1742116 reaction equation
C([O-])=O.[Na+].Cl[C:6]1[C:11]([N+:12]([O-])=O)=[CH:10][C:9]([C:15]([F:18])([F:17])[F:16])=[CH:8][C:7]=1[N+:19]([O-])=O.C([O-])(=O)C.[Na+].NC1C(N)=C(C(F)(F)F)C=CC=1>C(O)(=O)C.[Pd]>[NH2:19][C:7]1[CH:8]=[C:9]([C:15]([F:16])([F:17])[F:18])[CH:10]=[C:11]([NH2:12])[CH:6]=1

Participants

7

Reactant 4

HCID 98094-Chloro-3,5-dinitrobenzotrifluoride2×HCID 4367592,3-DiaminobenzotrifluorideHCID 517045Sodium AcetateHCID 2723810Sodium Formate

Product 1

HCID 677815-(Trifluoromethyl)benzene-1,3-diamineYield 45%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

Sodium formate (12.24 g) was added to a mixture of 4-chloro-3,5-dinitrobenzotrifluoride (5.41 g), sodium acetate (1.64 g) and 5% Pd/C (0.5 g) in glacial acetic acid (60 mL). The mixture was stirred and the resultant exotherm, which lasted about an hour, was controlled by cooling to maintain a reaction temperature of about 40° C. As the exotherm subsided, external heating was applied to maintain the temperature at about 40° C. Gas chromatographic analysis of the reaction mixture, at the end of one hour, indicated diaminobenzotrifluoride as the major component (35%) with no 4-chloro-3,5-dinitrobenzotrifluoride remaining. The maximum amount (about 45%) of 3,5-diaminobenzotrifluoride formed after 2 hours after which it was converted to other undesirable products.

Workup

  1. waitthe resultant exotherm, which lasted about an hour
  2. temperatureby cooling
  3. temperatureexternal heating
  4. temperatureto maintain the temperature at about 40° C
  5. customat the end of one hour

Sources & evidence

ORD record
ord-185781839bed40fca10d6de331075990
Source dataset
uspto-grants-1994_08
Patent number
US05336808

Reaction notes

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