Ethanol → Benzidine

HRID 260414

Reaction equation

HRID 260414 reaction equation
C(O)C.[H][H].[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)([O-])=O>[Pd].C1C=CC=CC=1>[NH2:6][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 152164,4'-Dinitro-1,1'-biphenylHCID 178418361HCID 178418361, compound2×HCID 178527255HCID 178527255, compound

Product 1

HCID 7111BenzidineYield 123.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 241BenzeneSolvent

Procedure

270 mg of 5%-Pd/C was suspended in 14 mL of a 1:1 mixed solvent of ethanol and benzene. While passing hydrogen through the system, a solution was added that consisted of 3.21 g of the 4,4'-dinitrobiphenyl-containing polysiloxane (average value of n: 14.4) synthesized in Reference Example 2 dissolved in 14 mL of the same mixed solvent. Hydrogen was injected into the system for 3 hours while stirring. The catalyst was then filtered off and the solvent was distilled under reduced pressure to give 3.00 g of the 4,4'-diaminobiphenyl-terminated polysiloxane as a viscous yellow liquid.

Workup

  1. additiona solution was added
  2. customsynthesized in Reference Example 2
  3. filtrationThe catalyst was then filtered off
  4. distillationthe solvent was distilled under reduced pressure

Sources & evidence

ORD record
ord-4959a58077c74bddb6fa89c41a33e44e
Source dataset
uspto-grants-1996_06
Patent number
US05527862

Linked notes

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