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

HRID 1905732Notes

Reaction equation

HRID 1905732 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-138ff54ca7e543bfa868cc6d2c4afe12
Source dataset
uspto-grants-1987_03
Patent number
US04647559

Reaction notes

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