Sodium Hydroxide → HCID 54549528, compound

HRID 636523Notes

Reaction equation

HRID 636523 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][C:14]=1[C:15](=[O:18])[NH:16][CH3:17])[CH:6]=[CH:7][C:8]([O:10]C)=[O:9].[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][C:14]=1[C:15](=[O:18])[NH:16][CH3:17])[CH:6]=[CH:7][C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54464795HCID 54464795, compound

Product 1

HCID 54549528HCID 54549528, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 3-methoxy-4-methylcarbamoylcinnamate (300 mg) in methanol was added 1N sodium hydroxide solution (1.5 ml) at ambient temperature, and the mixture was stirred at 50° C. for 5 hours. The solvent was distilled off, and the residue was dissolved in water. The solution was washed with diethyl ether, and adjusted to pH 4 with 1N hydrochloric acid. The resulting precipitates were collected by filtration and washed with water to give 3-methoxy-4-methylcarbamoylcinnamic acid (250 mg).

Workup

  1. distillationThe solvent was distilled off
  2. dissolutionthe residue was dissolved in water
  3. washThe solution was washed with diethyl ether
  4. customThe resulting precipitates
  5. filtrationwere collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-f3f609a69cbd4885b7bf97a3184b67cb
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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