Malonic Acid → (E)-3-(6-Acetamidopyridin-3-YL)acrylic acid

HRID 726316Notes

Reaction equation

HRID 726316 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=O)=[CH:7][N:6]=1)(=[O:3])[CH3:2].C(O)(=O)[CH2:14][C:15]([OH:17])=[O:16]>N1C=CC=CC=1.C(O)C>[C:1]([NH:4][C:5]1[N:6]=[CH:7][C:8](/[CH:11]=[CH:14]/[C:15]([OH:17])=[O:16])=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 867Malonic AcidHCID 22113222N-(5-Formylpyridin-2-yl)acetamide

Product 1

HCID 10703461(E)-3-(6-Acetamidopyridin-3-YL)acrylic acidYield 81.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

A mixture of 2-acetylamino-5-formylpyridine (241 mg) and malonic acid (168 mg) in pyridine (0.12 ml) and ethanol (0.36 ml) was refluxed for 2 hours. After cooling the mixture, the precipitate was collected by filtration, and washed with ethyl acetate to give (E)-3-(6-acetylamino-3-pyridyl)acrylic acid (248 mg) as a colorless powder.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureAfter cooling the mixture
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-73a629a20e844f1da33f5896eb8b6655
Source dataset
uspto-grants-1998_01
Patent number
US05708173

Reaction notes

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