Malonic Acid → 3-(6-Methyl-3-pyridyl)acrylic acid

HRID 1247893Notes

Reaction equation

HRID 1247893 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=O)=[CH:4][CH:3]=1.C(O)(=O)[CH2:11][C:12]([OH:14])=[O:13].N1CCCCC1>N1C=CC=CC=1>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[CH:11][C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 101925666-Methyl-3-pyridinecarboxaldehyde

Product 1

HCID 541408533-(6-Methyl-3-pyridyl)acrylic acidYield 59.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(a)(i) A mixture of 6-methylpyridine-3-carboxaldehyde (51.57 g), malonic acid (44.30 g), piperidine (6 ml) and pyridine (300 ml) was stirred at 100° for 3 hours and was allowed to cool. The mixture was evaporated to dryness, water was added to the residue and the solid which separated out was filtered off and recrystallised from ethanol-acetic acid to give 3-(6-methyl-3-pyridyl)acrylic acid (41.25 g) m.p. 213.5°-215.5°.

Workup

  1. temperatureto cool
  2. customThe mixture was evaporated to dryness, water
  3. additionwas added to the residue
  4. customthe solid which separated out
  5. filtrationwas filtered off
  6. customrecrystallised from ethanol-acetic acid

Sources & evidence

ORD record
ord-518238761e3e4d6eb575ec39ea670ac1
Source dataset
uspto-grants-1985_06
Patent number
US04521418

Reaction notes

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