Hydrochloric Acid → 3-[4-(Methylcarbamoyl)phenyl]prop-2-enoic acid

HRID 1604513Notes

Reaction equation

HRID 1604513 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]([CH:9]=[CH:10][C:11]([O:13]C)=[O:12])=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+].Cl>CO>[CH3:1][NH:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]([CH:9]=[CH:10][C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53693514Methyl 4-(methylcarbamoyl)cinnamate

Product 1

HCID 534120223-[4-(Methylcarbamoyl)phenyl]prop-2-enoic acidYield 79.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-(methylcarbamoyl)cinnamate (75 mg) in methanol (3 ml) was added 1 N aqueous sodium hydroxide solution (0.5 ml) at 40° C. The mixture was stirred at same temperature for 3 hours. 1 N-Hydrochloric acid (0.5 ml) was added to the reaction mixture and evaporated in vacuo. Water was added to the residue, the mixture was filtered and the residue was washed with diethyl ether to give 4-(methylcarbamoyl)cinnamic acid (56 mg) as a colorless powder.

Workup

  1. customevaporated in vacuo
  2. additionWater was added to the residue
  3. filtrationthe mixture was filtered
  4. washthe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-f3363c22e0d84c6fb375fc6d044c8fea
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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