Malonic Acid → 3-(4-Phenyl-3-pyridyl)acrylic acid

HRID 868351Notes

Reaction equation

HRID 868351 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[CH:13]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)[CH2:16][C:17]([OH:19])=[O:18].N1CCCCC1.N1C=CC=CC=1>C(OCC)C>[C:1]1([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[CH:13]=[CH:16][C:17]([OH:19])=[O:18])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 867Malonic AcidHCID 1049PyridineHCID 8082PiperidineHCID 131605444-Phenylpyridine-3-carbaldehyde

Product 1

HCID 539175383-(4-Phenyl-3-pyridyl)acrylic acidYield 64.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4.3 g of 4-phenyl-3-pyridinecarbaldehyde [cf. Heterocycles, 14, 813 (1980)], 2.5 g of malonic acid, 0.5 ml of piperidine, and 6 ml of pyridine is stirred at 100° C. for 2 hours. After cooling, 50 ml of diethyl ether is added, and the resulting precipitate is collected. The obtained solid is washed with water and dried to give 3.4 g of the title compound.

Workup

  1. temperatureAfter cooling
  2. customthe resulting precipitate is collected
  3. washThe obtained solid is washed with water
  4. customdried

Sources & evidence

ORD record
ord-f1e2ee7d3787457791a3e82c719d748a
Source dataset
uspto-grants-1988_10
Patent number
US04778796

Reaction notes

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