2-Propenoic acid, 3-(3-nitrophenyl)- → 3-(3-Aminophenyl)propionic acid

HRID 4287Notes

Reaction equation

HRID 4287 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[CH:7]=[CH:8][C:9]([OH:11])=[O:10])([O-])=O.[H][H]>C(O)(=O)C.CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 2

HCID 683902-Propenoic acid, 3-(3-nitrophenyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 27354063-(3-Aminophenyl)propionic acid

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A suspension of 100 g (0.52 moles) of 3-nitrocinnamic acid in 800 ml glacial acetic acid and 100 ml of methanol was hydrogenated at 50 pounds per square inch over 2.5 g 10% palladium on carbon until four equivalents of hydrogen were absorbed. The catalyst was filtered off, the filtrates combined and the solvent was concentrated in vacuo leaving a brown glass of 3-aminobenzenepropanoic acid. To this was added 1 liter of ethanolic hydrochloric acid which was brought to reflux for five hours. The solvent was evaporated off in vacuo leaving a purple solid. Recrystallization from ethyl acetate yielded 88.0 g of ethyl 3-aminobenzenepropanoate hydrochloride, mp 132°-135° C., (74% yield).

Workup

  1. customwere absorbed
  2. filtrationThe catalyst was filtered off
  3. concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-5738c90848c14330a8109484a074deed
Source dataset
uspto-grants-1988_02
Patent number
US04725602

Reaction notes

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