Malonic Acid → 2-Propenoic acid, 3-(5-fluoro-3-pyridinyl)-

HRID 868343Notes

Reaction equation

HRID 868343 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=O)[CH:5]=[N:6][CH:7]=1.C(O)(=O)[CH2:11][C:12]([OH:14])=[O:13].N1CCCCC1>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:11][C:12]([OH:14])=[O:13])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 141411595-Fluoropyridine-3-carbaldehyde

Product 1

HCID 27847502-Propenoic acid, 3-(5-fluoro-3-pyridinyl)-Yield 34%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1.1 g of the crude 5-fluoro-3-pyridinecarbaldehyde, 1.8 g of malonic acid, 0.15 ml of piperidine, and 7 ml of pyridine is stirred at 110° C. for 2 hours. The reaction mixture is concentrated, and 20 ml of water is added. The resulting precipitate is collected and washed with cold water to give 0.5 g of the title compound.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. addition20 ml of water is added
  3. customThe resulting precipitate is collected
  4. washwashed with cold water

Sources & evidence

ORD record
ord-398c328f6d974241a82489a18330cfbb
Source dataset
uspto-grants-1988_10
Patent number
US04778796

Reaction notes

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