Methyl 4-(2-nitroethenyl)benzoate → Methyl 4-(2-aminoethyl)benzoate

HRID 6732

Reaction equation

HRID 6732 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][N+:12]([O-])=O)=[CH:6][CH:5]=1.[H][H]>[Pd].C(O)C.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][NH2:12])=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 896295Methyl 4-(2-nitroethenyl)benzoateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 11183521Methyl 4-(2-aminoethyl)benzoateYield 103.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

Palladium on carbon (10%, 50 mg) was added to a solution of 4-(2-nitrovinyl)benzoic acid methyl ester (228 mg) in 5 mL of ethyl alcohol and 2 mL of acetic acid. The reaction vessel was saturated with hydrogen and stirred under a 1 atm hydrogen atmosphere for 20 h. The vessel was saturated with nitrogen and filtered through celite. Evaporation of the solvents gave 205 mg of crude 4-(2-amino-ethyl)-benzoic acid methyl ester.

Workup

  1. filtrationfiltered through celite
  2. customEvaporation of the solvents

Sources & evidence

ORD record
ord-dd260658769041a1a6db30df808d65ab
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Linked notes

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