Methyl Isobutyl Ketone → 5-Ethyl-2,3-pyridinedicarboxylic acid

HRID 1654997Notes

Reaction equation

HRID 1654997 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([C:12]([OH:14])=[O:13])[C:6]([C:9]([OH:11])=[O:10])=[N:7][CH:8]=1)[CH3:2].[CH2:15](C(C)=O)[CH:16](C)C>C(Cl)Cl>[CH2:1]([C:3]1[CH:4]=[C:5]([C:12]([OH:14])=[O:13])[C:6]([C:9]([OH:11])=[O:10])=[N:7][CH:8]=1)[CH3:2].[CH2:1]([C:3]1[CH:8]=[N:7][C:6]2[C:5]([CH:4]=1)=[CH:12][CH:16]=[CH:15][C:9]=2[OH:11])[CH3:2]

Participants

5

Reactant 2

HCID 7909Methyl Isobutyl KetoneHCID 1136065-Ethyl-2,3-pyridinedicarboxylic acid

Product 2

HCID 1136065-Ethyl-2,3-pyridinedicarboxylic acidHCID 117896928-Quinolinol, 3-ethyl-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Preparation of 5-ethyl-2,3-pyridinedicarboxylic acid ##STR6## The nitrate salt obtained in Example 1 is dispersed in a mixture of 100 mL of methylene chloride and 100 mL of methyl isobutyl ketone, heated at reflux temperature for 1 hour, cooled to room temperature and filtered. The filter cake is washed with a 1:1 mixture of methylene chloride:methyl isobutyl ketone and dried in vacuo to give 5-ethyl-2,3-pyridinedicarboxylic acid, 34.6 g, (89% isolated yield from 3-ethyl-8-hydroxyquinoline), 94.5% pure by HPLC.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 1 hour
  3. filtrationfiltered
  4. washThe filter cake is washed with a 1:1 mixture of methylene chloride
  5. dry with materialmethyl isobutyl ketone and dried in vacuo
  6. customto give

Sources & evidence

ORD record
ord-481e833f983f43439f019f5f82b4155c
Source dataset
uspto-grants-1995_04
Patent number
US05410062

Reaction notes

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