Hydrochloric Acid → 4-Propionamidocinnamic acid

HRID 1290214Notes

Reaction equation

HRID 1290214 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-904188cf1841443f8ba965bc1c7fbd99
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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