Lithium Hydroxide → 2-Chloro-6-(cyclopropylethynyl)nicotinic acid

Reaction equation

[Cl:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[CH:6][CH:5]=[C:4]([C:13]#[C:14][CH:15]2[CH2:17][CH2:16]2)[N:3]=1.[OH-].[Li+]>CO.O>[Cl:1][C:2]1[N:3]=[C:4]([C:13]#[C:14][CH:15]2[CH2:17][CH2:16]2)[CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9]

Participants

Procedure

The ester was hydrolyzed as follows: Ethyl 2-chloro-6-(2-cyclopropylethynyl)pyridine-3-carboxylate (0.7 g, 2.8 mmol) and lithium hydroxide (0.4 g, 16.86 mmol) were refluxed in a mixture of 30 mL MeOH and 10 mL water. The mixture was cooled and the methanol was removed in vacuo. The remaining solution was acidified to pH 2 with 1M HCl at 0° C. The precipitate was filtered and dried to give 0.4 g (57%) of the title compound. m/z=222.4 (M+1).