4'-Methyl-2-nitro-1,1'-biphenyl → 4'-Methyl-biphenyl-2-ylamine

HRID 1080734Notes

Reaction equation

HRID 1080734 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-])=O)=[CH:4][CH:3]=1>CO.[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 104431944'-Methyl-2-nitro-1,1'-biphenyl

Product 1

HCID 15108204'-Methyl-biphenyl-2-ylamineYield 93.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 15 g (70 mmol) of 4-methyl-2'-nitro-1,1'-biphenyl in 160 mL of methanol containing 900 mg of 5% palladium on carbon was hydrogenated for 1.5 hours at 40 psi. The reaction mixture was filtered through Celite and the filtrate evaporated under vacuum to yield 11.94 g (65.2 mmol, 93%) of the product. FAB-MS: calculated for C13H13N 183; found 184 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe filtrate evaporated under vacuum

Sources & evidence

ORD record
ord-13f49c8c109f4e9090d8c28dff77e98e
Source dataset
uspto-grants-1996_12
Patent number
US05583130

Reaction notes

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