Lithium Hydroxide → 4-(2-Methylpiperidin-1-yl)-3-nitrobenzoic acid

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A mixture of ethyl 4-fluoro-3-nitrobenzoate (Chontech 01072; 1.00 g; 4.69 mmol; 1 eq.) and 2-methylpiperidine (Aldrich M7, 280-3; 1.396 g; 14.07 mmol; 3 eq.) in DMF (4 mL) was stirred at 50° C. for 3 hours. The reaction was then allowed to return to room temperature and diluted with water. Extraction with ethyl acetate, drying over sodium sulfate and concentration in vacuo gave a yellow oil. The oil was taken up in THF (10 mL) and lithium hydroxide (561.73 mg; 23.46 mmol; 5 eq.) was added followed by water (10 mL). The reaction mixture was stirred at room temperature for 16 hours. After evaporation of the THF, the solution was diluted with water and washed with Et2O. The aqueous layer was acidified to pH 5 with AcOH, extracted with Et2O, dried over magnesium sulfate and concentrated in vacuo to afford the title compound (1.17 g, 94%) as a yellow solid.

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