1,1'-Biphenyl, 3-nitro- → 3-Aminobiphenyl

HRID 612340

Reaction equation

HRID 612340 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>CO.C(Cl)(Cl)Cl.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 164501,1'-Biphenyl, 3-nitro-

Product 1

HCID 167173-AminobiphenylYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584188Chloroform methanolSolvent

Procedure

A mixture of 3-nitrobiphenyl (20 g, 100 mmol) and 10% Pd/C (2 g) in MeOH/CHCl3 (300 mL, 1:1) is hydrogenated at 40 psi for 4 hours. The mixture is suction filtered through a layer of diatomaceous earth and washed with MeOH. The filtrate is evaporated to dryness and the solid is further dried under vacuum to give 16 g (95%) of 3-aminobiphenyl.

Workup

  1. filtrationfiltered through a layer of diatomaceous earth
  2. washwashed with MeOH
  3. customThe filtrate is evaporated to dryness
  4. customthe solid is further dried under vacuum

Sources & evidence

ORD record
ord-d58c166ee3b949b489661f1f73bb36cb
Source dataset
uspto-grants-1999_12
Patent number
US06004536

Linked notes

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