Sodium Hydroxide → 3-Fluoro-4-(4-methylpiperazin-1-yl)benzoic acid

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Reaction Conditions

Reaction Steps

To methyl 3-fluoro-4-(4-methylpiperazin-1-yl)benzoate (1.80 g, 7.13 mmol) in methanol (40 ml) was added 1 M sodium hydroxide (25 ml, 25.0 mmol). The solution was stirred at 50° C. for 3 h, at which point the mixture was concentrated. The residue was diluted with water (10 ml) and the pH adjusted to 6 with 1 N hydrochloric acid. The resultant precipitate was collected by filtration and dried in vacuo to afford (733 mg, 43%) of 3-fluoro-4-(4-methylpiperazin-1-yl)benzoic acid. 1H NMR (400 MHz, CD3OD): 7.73-7.68 (d, 1H), 7.62-7.57 (d, 1H), 7.03-6.97 (m, 1H), 3.26-3.20 (m, 4H), 2.83-2.76 (m, 4H), 2.47 (s, 3H). MS (EI) for C12H15FN2O2: 239 (MH+).

Provenance & Evidence