Ethyl (E)-2-methyl-3-(4-nitrophenyl)prop-2-enoate → Ethyl 3-(4-aminophenyl)-2-methylpropanoate

HRID 445828Notes

Reaction equation

HRID 445828 reaction equation
[CH3:1]/[C:2](=[CH:8]\[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1)/[C:3]([O:5][CH2:6][CH3:7])=[O:4].[H][H]>C(O)C.[Pd]>[NH2:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH:2]([CH3:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 11241815Ethyl (E)-2-methyl-3-(4-nitrophenyl)prop-2-enoateHCID 178418361HCID 178418361, compound

Product 1

HCID 46941402Ethyl 3-(4-aminophenyl)-2-methylpropanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (E)-ethyl 2-methyl-3-(4-nitrophenyl)acrylate (645) (2.49 g, 10.6 mmol) in ethanol (100 mL) was added Pd/C (250 mg, 10% Degussa type). A balloon of hydrogen gas was added and the reaction was evacuated and back-filled with hydrogen three times. The reaction was stirred overnight at room temperature, was filtered through a pad of celite and concentrated in vacuo to give ethyl 3-(4-aminophenyl)-2-methylpropanoate (646).

Workup

  1. customthe reaction was evacuated
  2. additionback-filled with hydrogen three times
  3. filtrationwas filtered through a pad of celite
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-457a7e326d2e4244a1e3b13121ccd7f2
Source dataset
uspto-grants-2013_07
Patent number
US08476308B2

Reaction notes

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