Ammonium formate → 4-(2-Methoxyphenyl)aniline

HRID 25747Notes

Reaction equation

HRID 25747 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 131434782-Methoxy-4'-nitro-1,1'-biphenyl

Product 1

HCID 27595594-(2-Methoxyphenyl)anilineYield 107.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 52.4 g of 2-methoxy-4′-nitrobiphenyl and 76 g of ammonium formate in 640 mL of methanol was treated with 6.4 g of 10% Pd/C at 0° C. The reaction mixture was allowed to stir at the same temperature for half an hour. The reaction was then warmed to room temperature and the mixture was allowed to stir overnight. The reaction mixture was filtered through diatomaceous earth and the residue was rinsed with methanol. The methanol was evaporated in vacuo and the remaining mixture was dissolved in EtOAc and washed with water several times. The organic layer was dried over magnesium sulfate. The solvent was evaporated in vacuo and yielded 49 g of 2-methoxy-4′-aminobiphenyl as a solid.

Workup

  1. stirringto stir overnight
  2. filtrationThe reaction mixture was filtered through diatomaceous earth
  3. washthe residue was rinsed with methanol
  4. customThe methanol was evaporated in vacuo
  5. dissolutionthe remaining mixture was dissolved in EtOAc
  6. washwashed with water several times
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-432959d9804940648e5102cf96e48dea
Source dataset
uspto-grants-2005_02
Patent number
US06858627B2

Reaction notes

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