[C:1]([C:5]1[CH:6]=[C:7]([C:10]([O:13][CH3:14])=[CH:11][N:12]=1)[C:8]#N)([CH3:4])([CH3:3])[CH3:2].[OH-:15].[Na+].S(=O)(=O)(O)[OH:18]>OP([O-])(O)=O.[K+]>[C:1]([C:5]1[CH:6]=[C:7]([C:10]([O:13][CH3:14])=[CH:11][N:12]=1)[C:8]([OH:18])=[O:15])([CH3:4])([CH3:3])[CH3:2]The above nitrile (1.10 g, 5.68 mmol) was dissolved in aqueous sulfuric acid (9.0 M in water, 6.0 mL) and heated to 120° C. for 8 h. The solution was cooled to room temperature and NaOH (˜2.0 g) was added slowly to neutralize the solution. The mixture was then diluted with an equal volume of saturated aqueous KH2PO4 and extracted several times with 25% 2-propanol in chloroform. The extracts were combined, dried over sodium sulfate, filtered, and concentrated in vacuo to provide 2-tert-butyl-5-methoxy-isonicotinic acid (1.09 g, 92%) as a pale brown solid which was utilized without further purification.
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