Sodium Hydroxide → 4-Chloro-3,5-dimethylpicolinic Acid
Reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([C:9]([O:11]CC)=[O:10])[C:3]=1[CH3:14].[OH-].[Na+]>>[C:9]([C:4]1[C:3]([CH3:14])=[C:2]([Cl:1])[C:7]([CH3:8])=[CH:6][N:5]=1)([OH:11])=[O:10]Participants
3
Procedure
4-Chloro-2-Ethoxycarbonyl-3,5-Lutidine (1 eq.) was suspended in 10% sodium hydroxide aqueous solution (4 eq.), the mixture was stirred and heated to 80ℑ C. After 4 hours a homogeneoussolution was obtained. The solution was washed with toluene and then acidified to pH 2.5. The white precipitate was extracted with dichloromethane (3×5 volumes). The combined organic extracts were dried over sodium sulfate, filtered and the solvent was evaporated under vacuum. The 2-carboxy-4-chloro-3,5-lutidine product was obtained as an off white solid in 85% yield.
Workup
- temperatureheated to 80ℑ C
- customAfter 4 hours a homogeneoussolution was obtained