Malonic Acid → 3-(6-Methyl-3-pyridyl)acrylic acid

HRID 868341Notes

Reaction equation

HRID 868341 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=O)=[CH:4][CH:3]=1.C(O)(=O)[CH2:11][C:12]([OH:14])=[O:13].N1CCCCC1>N1C=CC=CC=1>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[CH:11][C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 101925666-Methyl-3-pyridinecarboxaldehyde

Product 1

HCID 541408533-(6-Methyl-3-pyridyl)acrylic acidYield 81.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4.2 g of the crude 6-methyl-3-pyridinecarbaldehyde, 7.2 g of malonic acid, 0.5 ml of piperidine, and 25 ml of pyridine is stirred at 100° C. for 3 hours. The reaction mixture is concentrated, and 5 ml of water is added. The resulting precipitate is collected to give 4.6 g of the title compound. m.p. 221°-222° C.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. addition5 ml of water is added
  3. customThe resulting precipitate is collected

Sources & evidence

ORD record
ord-268d68c3999e4cdcaf8b602dc9e5bd1c
Source dataset
uspto-grants-1988_10
Patent number
US04778796

Reaction notes

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