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

HRID 1719151Notes

Reaction equation

HRID 1719151 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]>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

4

Reactant 2

HCID 867Malonic AcidHCID 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 (discarded). The aqueous phase was acidified with hydrochloric acid and was extracted with chloroform. The 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°-158°. This acid was esterified using ethanol and sulphuric acid to give the ethyl ester m.p. 85°-88°.

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 (discarded)
  6. extractionwas extracted with chloroform
  7. washThe chloroform extracts were washed with water
  8. customevaporated

Sources & evidence

ORD record
ord-98eb4a6b8026441aa8710512dc12d512
Source dataset
uspto-grants-1985_09
Patent number
US04539207

Reaction notes

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