Hydrochloric Acid → 4-Propionamidocinnamic acid

HRID 864571Notes

Reaction equation

HRID 864571 reaction equation
[C:1]([NH:5][C:6]1[CH:18]=[CH:17][C:9]([CH:10]=[CH:11][C:12]([O:14]CC)=[O:13])=[CH:8][CH:7]=1)(=[O:4])[CH2:2][CH3:3].[OH-].[Na+].Cl>C(O)C>[C:1]([NH:5][C:6]1[CH:18]=[CH:17][C:9]([CH:10]=[CH:11][C:12]([OH:14])=[O:13])=[CH:8][CH:7]=1)(=[O:4])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54078953Ethyl 4-propionamidocinnamate

Product 1

HCID 538191414-Propionamidocinnamic acidYield 81.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-propionamidocinnamate (160 mg) in ethanol (5 ml) was added 1N aqueous sodium hydroxide solution (1.5 ml) at ambient temperature. The mixture was stirred at same temperature for 14 hours, and then at 40° C. for 2 hours. 1N-hydrochloric acid (1.5 ml) was added to the reaction mixture and evaporated in vacuo. The residue was diluted with 10% methanol-dichloromethane, washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from diisopropyl ether to give 4-propionamidocinnamic acid (115 mg) as a colorless powder.

Workup

  1. waitat 40° C. for 2 hours
  2. customevaporated in vacuo
  3. additionThe residue was diluted with 10% methanol-dichloromethane
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-5dde0a5afc354b1db32138c8cfa71fdf
Source dataset
uspto-grants-1996_10
Patent number
US05563162

Reaction notes

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