Malonic Acid → 3-(2-Chloro-5,6-dimethyl-3-pyridyl)acrylic acid

HRID 903346Notes

Reaction equation

HRID 903346 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=O)=[CH:6][C:5]([CH3:10])=[C:4]([CH3:11])[N:3]=1.C(O)(=O)[CH2:13][C:14]([OH:16])=[O:15].N1CCCCC1>N1C=CC=CC=1>[Cl:1][C:2]1[C:7]([CH:8]=[CH:13][C:14]([OH:16])=[O:15])=[CH:6][C:5]([CH3:10])=[C:4]([CH3:11])[N:3]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 127838462-Chloro-5,6-dimethylnicotinaldehyde

Product 1

HCID 541670373-(2-Chloro-5,6-dimethyl-3-pyridyl)acrylic acidYield 87%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-chloro-5,6-dimethyl-3-pyridinecarboxaldehyde (16.85 g), malonic acid (11.45 g), piperidine (10 ml) and pyridine (100 ml) was heated under reflux for 1 hour and evaporated to an oil. This oil was dissolved in sodium hydroxide solution and was extracted with chloroform, the residual aqueous phase was acidified with hydrochloric acid and extracted with chloroform. The second chloroform extracts were washed with water and evaporated to give 3-(2-chloro-5,6-dimethyl-3-pyridyl)acrylic acid (18.3 g, 87%), m.p. 150°-8°. This acid was esterified using ethanol and sulphuric acid to give the ethyl ester, m.p. 85°-8°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. customevaporated to an oil
  4. dissolutionThis oil was dissolved in sodium hydroxide solution
  5. extractionwas extracted with chloroform
  6. extractionextracted with chloroform
  7. washThe second chloroform extracts were washed with water
  8. customevaporated

Sources & evidence

ORD record
ord-a5e2e799e9b945ebae2b37045103fdc0
Source dataset
uspto-grants-1980_10
Patent number
US04227000

Reaction notes

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