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

HRID 1485353Notes

Reaction equation

HRID 1485353 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-6311e7149d984e5b8aac43a0aa4de080
Source dataset
uspto-grants-2016_08
Patent number
US09422293B2

Reaction notes

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