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

HRID 865876Notes

Reaction equation

HRID 865876 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 pH 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-3369606ef96444c7b32365b12580eab4
Source dataset
uspto-grants-1996_10
Patent number
US05567841

Reaction notes

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