Malonic Acid → 3-(2-Pyridyl)acrylic acid

HRID 2307412Notes

Reaction equation

HRID 2307412 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.C(O)(=O)[CH2:10][C:11]([OH:13])=[O:12]>N1C=CC=CC=1.N1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[CH:10][C:11]([OH:13])=[O:12]

Participants

5

Reactant 2

HCID 867Malonic AcidHCID 142732-Pyridinecarboxaldehyde

Product 1

HCID 2478243-(2-Pyridyl)acrylic acid

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 31268PyrrolidineSolvent

Procedure

A mixture of pyridine-2-carboxaldehyde (32.1 g 0.30 mmol), malonic acid (62.4 g, 0.60 mmol) in pyridine (200 mL) and pyrrolidine (2 mL) was stirred under reflux for 16 hours. The reaction mixture was allowed to cool to room temperature and poured into ice water (200 mL). The aqueous layer was extracted with CH2Cl2 (2×100 mL). The combined organic layer was concentrated in vacuo and the crude material obtained was purified by flash column chromatography on silica using a gradient system of solvents: 1) ethyl acetate (100%); 2) methanol/ethyl acetate (10%). The title product was obtained (6.28 g, 14%) as a grayish-green solid.

Workup

  1. temperatureunder reflux for 16 hours
  2. extractionThe aqueous layer was extracted with CH2Cl2 (2×100 mL)
  3. concentrationThe combined organic layer was concentrated in vacuo
  4. customthe crude material obtained
  5. customwas purified by flash column chromatography on silica using a gradient system of solvents

Sources & evidence

ORD record
ord-1cb936644af94698b65ff833e07b01ef
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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