Hydrazine hydrate (1:1) → HCID 59144174, compound

Participants

Reaction Steps

To a stirred solution of N,N-diethyl-2-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethanamine (1.109 g, 3.76 mmol) in MeOH (30 mL) was added Raney-Nickel (slurry in water; ˜0.1 g, 3.76 mmol) followed by hydrazine hydrate (1.828 mL, 37.6 mmol). The mixture was immersed in a preheated oil bath and refluxed for 30 minutes. The solution was cooled to room temperature, filtered through Celite, and washed with MeOH. The crude material was filtered through a silica plug (3.5% (2M NH3 in MeOH):CH2Cl2). The solvent was evaporated to give the product as dark brown oil (1.07 g, quantitative). 1H NMR (CDCl3) δ 6.58 (d, J=8.7 Hz, 1H), 6.45 (d, J=2.7 Hz, 1H), 6.40 (dd, J=2.7, 8.7 Hz, 1H), 3.53-3.50 (m, 2H), 3.30 (m, 4H), 3.03-2.99 (m, 2H), 1.03 (t, J=7.2 Hz, 6H); ESI-MS (m/z, %): 268, 266 (MH+, 100), 100 (52).

Provenance & Evidence