Sodium Hydroxide → HCID 21904722, compound

Reaction equation

[F:1][C:2]([F:20])([F:19])[C:3]1[C:4]([N:9]2[CH2:14][CH:13]=[C:12]([C:15]([O:17]C)=[O:16])[CH2:11][CH2:10]2)=[N:5][CH:6]=[CH:7][CH:8]=1.[OH-].[Na+]>C1COCC1.O>[F:19][C:2]([F:1])([F:20])[C:3]1[C:4]([N:9]2[CH2:10][CH:11]=[C:12]([C:15]([OH:17])=[O:16])[CH2:13][CH2:14]2)=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

Procedure

Methyl 3′-(trifluoromethyl)-3,6-dihydro-2H-1,2′-bipyridine-4-carboxylate (15 mL) in THF (30 mL) was treated with 1N NaOH (27 mL) and stirred for 2 hours. The mixture was treated with additional 1N NaOH (16 mL), stirred for 1 hour, treated with 1N NaOH (14.5 mL), and stirred for 1 hour. The mixture was diluted with water and extracted with CH2Cl2. The aqueous layer was then acidified with concentrated HCl and extracted with CHCl3. The organic layer was dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure to provide the title compound.