Ethanol → Ethyl 2-amino-6-chloropyridine-4-carboxylate
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[N:10]=1)[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH2:16](O)[CH3:17]>>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[N:10]=1)[C:5]([O:7][CH2:16][CH3:17])=[O:6]Participants
4
Procedure
2-Amino-6-chloroisonicotinic acid (500 mg, 2.90 mmol) was dissolved in ethanol (29.0 mL), and the solution was stirred under heat and reflux for 3 hours after adding thionyl chloride (1.06 mL, 14.5 mmol). The solvent was then evaporated under reduced pressure. The residue was extracted with chloroform after adding a sodium hydrogen carbonate aqueous solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give ethyl 2-amino-6-chloroisonicotinate (510 mg, yield 88%).