Hydrochloric Acid → (1,1'-Biphenyl)-4,4'-diamine, 2,2'-bis(trifluoromethyl)-

HRID 745142

Reaction equation

HRID 745142 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].Cl>C(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 2

HCID 313Hydrochloric AcidHCID 113724052,2'-Bis(trifluoromethyl)-4,4'-dinitrobiphenyl

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Stannous chloride dihydrate (8 g) was added to a solution of 2,2'-bis(trifluoromethyl)-4,4'-dinitro-1,1'-biphenyl (1.9 g) in 5 ml of ethanol. Concentrated hydrochloric acid (12 ml) was added carefully to the mixture while stirring at room temperature. The mixture was refluxed overnight and the ethanol was removed. Water was added to the residue and it was made basic with 20% sodium hydroxide solution. The resulting white precipitate was collected by filtration, washed with water, dried and then extracted in a Soxhlet flask with acetone for four hours. Removal of acetone gave a white residue, 2,2'-bis(trifluoromethyl)-4,4'-diamino-1,1'-biphenyl, ##STR7## which was recrystallized from chloroform-hexane to give 1.2 g (74% yield) of short white needles, m.p. 185°-186° C.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customthe ethanol was removed
  3. additionWater was added to the residue and it
  4. filtrationThe resulting white precipitate was collected by filtration
  5. washwashed with water
  6. customdried
  7. extractionextracted in a Soxhlet flask with acetone for four hours
  8. customRemoval of acetone

Sources & evidence

ORD record
ord-abbfb463c6e041c4aa74df0d48b07a2c
Source dataset
uspto-grants-1986_07
Patent number
US04597891

Linked notes

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