2,2'-Bis(trifluoromethyl)-4,4'-dinitrobiphenyl → (1,1'-Biphenyl)-4,4'-diamine, 2,2'-bis(trifluoromethyl)-

HRID 1828612Notes

Reaction equation

HRID 1828612 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][C:13]=1[C:21]([F:24])([F:23])[F:22]>[Pd].C(OCC)(=O)C>[F:1][C:2]([F:25])([F:26])[C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:13]=1[C:21]([F:22])([F:23])[F:24]

Participants

4

Reactant 1

HCID 113724052,2'-Bis(trifluoromethyl)-4,4'-dinitrobiphenyl

Product 1

HCID 629349(1,1'-Biphenyl)-4,4'-diamine, 2,2'-bis(trifluoromethyl)-Yield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A hydrogenation bottle was charged with 40.0 g of 2,2′-bis(trifluoromethyl)-4,4′-dinitrobiphenyl, 0.6 g of 5% palladium on activated carbon and 200 ml of ethyl acetate. The bottle was secured on a Parr hydrogenation apparatus, flushed five times with hydrogen, and then pressurized with hydrogen to 56 psi. The pressure was maintained, and the vessel was agitated for several hours. After the reaction mixture was filtered and about 200 ml of hexanes were added. The crystals that formed were filtered to afford 30.2 g (90%) of product.

Workup

  1. customflushed five times with hydrogen
  2. temperatureThe pressure was maintained
  3. filtrationAfter the reaction mixture was filtered
  4. additionabout 200 ml of hexanes were added
  5. customThe crystals that formed
  6. filtrationwere filtered

Sources & evidence

ORD record
ord-cab769b5f6f141da8cfcfadba3cea32d
Source dataset
uspto-grants-2006_06
Patent number
US07058249B2

Reaction notes

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