Hydrazine hydrate (1:1) → 4-(2-(Pyrrolidin-1-yl)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amine

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To a solution of 7-nitro-4-(2-(pyrrolidin-1-yl)ethyl)-3,4-dihydro-2H-benzo[b][1,4]thiazine (0.637 g, 2.172 mmol) in MeOH (30 mL) was added Raney-Nickel (slurry in water) (˜30 mg, 2.172 mmol) followed by hydrazine hydrate (1.056 mL, 21.72 mmol), and the mixture was immersed in a preheated oil bath and refluxed for 1 hour. The solution was cooled to room temperature, filtered through a pad of Celite, and washed with 100 mL of MeOH. The crude material was filtered through a silica plug (3.5-10% 2M NH3 in MeOH/CH2Cl2). The solvent was evaporated to give the title product as a dark brown oil (0.61 g, quantitative). 1H NMR (DMSO-d6) δ 6.49 (d, J=8.7 Hz, 1H), 6.26-6.23 (m, 2H), 4.42 (brs, 2H), 3.38-3.35 (m, 2H), 3.21 (t, J=7.2 Hz, 2H), 2.97-2.94 (m, 2H), 2.55 (t, J=7.2 Hz, 2H), 2.45 (brs, 4H), 1.66 (brs, 4H); ESI-MS (m/z, %): 266, 264 (MH+, 100), 98 (34).

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