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

HRID 1904021Notes

Reaction equation

HRID 1904021 reaction equation
[CH3:1][C:2]([C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1)([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4]>C(O)C.[Pd]>[NH2:15][C:12]1[CH:11]=[CH:10][C:9]([C:2]([CH3:1])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:14][CH:13]=1

Participants

4

Reactant 1

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

Product 1

HCID 15544083Ethyl 2-(4-aminophenyl)-2-methylpropanoateYield 47%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In 120 ml of ethanol, 20.33 g of the ester obtained above was hydrogenated with 0.3 g of palladium black catalyst. The palladium catalyst was filtered off and the ethanol was distilled off in vacuo. The residue was taken up in 5% hydrochloric acid and washed with ethyl acetate. The separated water layer was neutralized with sodium carbonate and extracted with ethyl acetate. After the ethyl acetate layer was dried over sodium sulfate, the ethyl acetate was distilled off in vacuo and the residue was subjected to silica gel chromatography using chloroform as a solvent to give 8.31 g (0.04 mole, 47% yield) of ethyl 2-(4-aminophenyl)-2-methylpropionate.

Workup

  1. filtrationThe palladium catalyst was filtered off
  2. distillationthe ethanol was distilled off in vacuo
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. dry with materialAfter the ethyl acetate layer was dried over sodium sulfate
  6. distillationthe ethyl acetate was distilled off in vacuo

Sources & evidence

ORD record
ord-3f12e798bf0f40199aa23c8ff6df9022
Source dataset
uspto-grants-1984_03
Patent number
US04439448

Reaction notes

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