Dichloromethane → 5-Ethyl-2,3-pyridinedicarboxylic acid

HRID 1975244Notes

Reaction equation

HRID 1975244 reaction equation
[N+]([O-])([O-])=O.[C:5]([C:8]1[C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]([CH2:17][CH3:18])=[CH:10][NH+:9]=1)([OH:7])=[O:6].C(Cl)Cl.[CH2:22](C(C)=O)[CH:23](C)C>>[CH2:17]([C:11]1[CH:12]=[C:13]([C:14]([OH:16])=[O:15])[C:8]([C:5]([OH:7])=[O:6])=[N:9][CH:10]=1)[CH3:18].[CH2:17]([C:11]1[CH:10]=[N:9][C:8]2[C:13]([CH:12]=1)=[CH:14][CH:23]=[CH:22][C:5]=2[OH:7])[CH3:18]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7909Methyl Isobutyl KetoneHCID 20077541HCID 20077541, compound

Product 2

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

Procedure

The nitrate salt obtained in Example 1 is dispersed in a mixture of lo0 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-fdfe059635a74a75b85a97d52252d7d8
Source dataset
uspto-grants-1994_02
Patent number
US05284955

Reaction notes

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