Hydrochloric Acid → Ethyl 3-(4-aminophenyl)propanoate

HRID 865874Notes

Reaction equation

HRID 865874 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1)([O-])=O.Cl>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 1268038Ethyl 4-nitrocinnamate

Product 1

HCID 10442595Ethyl 3-(4-aminophenyl)propanoateYield 86.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 500 mL Parr hydrogenation vessel was charged with 12.36 g (55.9 mmol) of (E)-3-(4-nitrophenyl)-2-propenoic acid, ethyl ester, 100 mL of absolute ethanol, 15 mL of concentrated hydrochloric acid and 0.75 g of 10% palladium-on-activated charcoal. The slurry was purged with nitrogen and then agitated under an initial pressure of 44.5 psi of hydrogen gas. After 16 h, 18.5 psi had been consumed. The flask was evacuated, purged again with nitrogen and the contents filtered through Celite and evaporated. The residue was dissolved in water and adjusted to pH 9 with solid sodium carbonate. The resulting mixture was extracted thrice with dichloromethane, and the combined organic extracts dried over Na2SO4, filtered and evaporated to provide 9.31 g, 86% of title compound as a yellow oil, sufficiently pure for use in subsequent reactions.

Workup

  1. customThe slurry was purged with nitrogen
  2. custom18.5 psi had been consumed
  3. customThe flask was evacuated
  4. custompurged again with nitrogen
  5. filtrationthe contents filtered through Celite
  6. customevaporated
  7. dissolutionThe residue was dissolved in water
  8. extractionThe resulting mixture was extracted thrice with dichloromethane
  9. dry with materialthe combined organic extracts dried over Na2SO4
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-02160299d3c54aa2af4241ff66fb06d2
Source dataset
uspto-grants-1996_10
Patent number
US05567841

Reaction notes

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