Hydrochloric Acid → Ethyl 3-(3-Aminophenyl)propionate

HRID 727511Notes

Reaction equation

HRID 727511 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 5354248Ethyl 3-nitrocinnamate

Product 1

HCID 82314Ethyl 3-(3-Aminophenyl)propionateYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A Parr hydrogenation vessel was charged with Part (1) compound (12.0 g, 54.3 mmol), concentrated HCl (15 mL, 0.15 mmol), 10% palladium on carbon (750 mg) and absolute ethanol (75 mL). The slurry was purged with nitrogen and agitated under an initial pressure of 45 psi of hydrogen gas. After 16 h, the flask was evacuated and the contents filtered through Celite and evaporated. The residue was dissolved in water and adjusted to DH 9 with solid sodium carbonate. The resulting mixture was extracted with dichloromethane (250 mL×2). The combined extracts were evaporated to give the title compound (8.7 g, 86%) as an oil.

Workup

  1. customThe slurry was purged with nitrogen
  2. customthe flask was evacuated
  3. filtrationthe contents filtered through Celite
  4. customevaporated
  5. dissolutionThe residue was dissolved in water
  6. extractionThe resulting mixture was extracted with dichloromethane (250 mL×2)
  7. customThe combined extracts were evaporated

Sources & evidence

ORD record
ord-de655e51b90f4f868315593943ffde11
Source dataset
uspto-grants-1998_01
Patent number
US05712396

Reaction notes

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