Ethyl 2-methyl-2-(4-nitrophenyl)propanoate → Ethyl 2-(4-aminophenyl)-2-methylpropanoate

HRID 1005426Notes

Reaction equation

HRID 1005426 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]([CH3:16])([CH3:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 15544079Ethyl 2-methyl-2-(4-nitrophenyl)propanoate

Product 1

HCID 15544083Ethyl 2-(4-aminophenyl)-2-methylpropanoateYield 91.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of ethyl (4-nitrophenyl)-2,2-dimethylacetate (3.30 g, 13.9 mmol) and 10% Pd/C in methanol (40 mL) was hydrogenated in a Parr apparatus at 50 psi for 2 hours. The catalyst was removed by filtration, and the solvent was evaporated to give ethyl (4-aminophenyl)-2,2-dimethylacetate (2.63 g, 91%) as a colorless oil.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2e408ce3b3e54c39914442366c7586d4
Source dataset
uspto-grants-2000_04
Patent number
US06054470

Reaction notes

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