Water → 3-Methyl-isonicotinic acid

HRID 342516

Reaction equation

HRID 342516 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[C:3]([CH3:8])[CH:2]=1.[Se](=O)=[O:10].[OH2:12]>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:8][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][C:4]=1[C:7]([OH:10])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 114173,4-DimethylpyridineHCID 24007Selenium Dioxide

Product 1

HCID 15020033-Methyl-isonicotinic acidYield 44%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
185 °C

Procedure

To a hot (155° C.) solution of 10.7 g (0.1 mol) of 3,4-lutidine in 100 mL diphenylether, was added 18 g (0.16 mol) selenium dioxide in portions. After about 20 minutes, the reaction was heated to 185° C. and allowed to react for approximately thirty minutes. After cooling, the reaction mixture was diluted with water and filtered. The filtrate was extracted with chloroform and the chloroform extracts were then concentrated under reduced pressure to provide 6.0 g of a pale brown solid.

Workup

  1. customto react for approximately thirty minutes
  2. temperatureAfter cooling
  3. filtrationfiltered
  4. extractionThe filtrate was extracted with chloroform
  5. concentrationthe chloroform extracts were then concentrated under reduced pressure

Sources & evidence

ORD record
ord-a8834cd904fd4485adfbfb930d8009fd
Source dataset
uspto-grants-1999_01
Patent number
US05859002

Linked notes

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