Ammonium formate → Methyl 2-(4-aminophenyl)-2-methylpropanoate

HRID 1186123Notes

Reaction equation

HRID 1186123 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]([CH3:15])([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1)[CH3:5].C([O-])=O.[NH4+]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:16])[C:4]([C:6]1[CH:7]=[CH:8][C:9]([NH2:12])=[CH:10][CH:11]=1)([CH3:15])[CH3:5]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 11299024HCID 11299024, compound

Product 1

HCID 584407Methyl 2-(4-aminophenyl)-2-methylpropanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-methyl-2-(4-nitrophenyl)-propionic acid methyl ester (932.2 mg, 4.16 mmol) and ammonium formate (1.58 g, 25.1 mmol) in MeOH was added Pd/C (10%, 441.2 mg, 0.414 mmol). The reaction mixture was stirred at rt until gas evolution ceased, then filtered through a plug of diatomaceous earth and concentrated. The residue was redissolved in H2O and extracted with EtOAc. The organic layers were combined, dried, and concentrated to provide the title compound which was used without further purification.

Workup

  1. filtrationfiltered through a plug of diatomaceous earth
  2. concentrationconcentrated
  3. dissolutionThe residue was redissolved in H2O
  4. extractionextracted with EtOAc
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-76e05e64b2bf4e0e9a52808606d11430
Source dataset
uspto-grants-2014_03
Patent number
US08673895B2

Reaction notes

Loading…