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

HRID 224857Notes

Reaction equation

HRID 224857 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 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 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. filtrationthe solid was filtered off
  5. customrecrystallised from ethanol-acetic acid

Sources & evidence

ORD record
ord-f8a8ef771ae54d769fd408a08825a199
Source dataset
uspto-grants-1980_11
Patent number
US04234588

Reaction notes

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