2-Pyridone → 2-Cyano-3-(4-methoxyphenyl)prop-2-enoic acid

HRID 2232238Notes

Reaction equation

HRID 2232238 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].[C:16]([CH2:18][C:19]([OH:21])=[O:20])#[N:17].N1C=CC=CC1=O>C1(C)C=CC=CC=1.O>[C:16]([C:18](=[CH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1)[C:19]([OH:21])=[O:20])#[N:17]

Participants

7

Reactant 4

HCID 88712-PyridoneHCID 9740Cyanoacetic acidHCID 312444-MethoxybenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 2332602-Cyano-3-(4-methoxyphenyl)prop-2-enoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A stirred mixture of p-anisaldehyde (60.7 ml), ammonium acetate (7.5 g), cyanoacetic acid (42.5 g), pyridone (70 ml) in toluene (390 ml) is refluxed using a Dean Stark trap until about 9 ml of water is collected. The reaction mixture is cooled and the solid precipitate filtered and stirred with 10% aqeuous HCL. The solid is filtered and recrystallized from methanol yielding the desired product.

Workup

  1. temperatureis refluxed
  2. customis collected
  3. temperatureThe reaction mixture is cooled
  4. filtrationthe solid precipitate filtered
  5. filtrationThe solid is filtered
  6. customrecrystallized from methanol yielding the desired product

Sources & evidence

ORD record
ord-dfafc222ec5049a987a6f8bb04440957
Source dataset
uspto-grants-1988_11
Patent number
US04788187

Reaction notes

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