[CH3:1][C:2]1[N:7]=C(C#N)[CH:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].C[C:14]([CH3:17])([O-:16])C.[K+].CC([OH:22])C>O>[CH3:1][C:2]1[N:7]=[C:17]([C:14]([OH:22])=[O:16])[CH:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]To a solution of 6-methyl-5-nitropicolinonitrile (31B, 500 mg, 3.1 mmol) in 2-propanol (1 mL) and water (5 mL) was added potassium tert-butoxide (687 mg, 6.13 mmol). The mixture was stirred at 100° C. overnight, when LCMS indicated that the reaction was complete. The mixture diluted with water, and then extracted with DCM (10 mL×3). The aqueous phase was acidified with 1N HCl solution, and extracted with DCM. The organic layer was dried and concentrated to give the crude product which was used to the next step without further purification. LC-MS: m/z 181 (M−H)+
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