Hydrazine hydrate (1:1) → 2-Amino-5-nitrobenzenethiol

Participants

Reaction Steps

To a solution of 6-Nitrobenzo[d]thiazole (5a) (10 g, 55.5 mmol) in EtOH (100 mL), Hydrazine hydrate (39 g, 77.9 mmol) was added at room temperature under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 4 h. After completion of the reaction (by TLC) the volatiles were removed under reduced pressure, the residue was neutralized with 1N HCl (100 mL) and extracted with EtOAc (3×150 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to afford 2-Amino-5-nitrobenzenethiol (5b) (7.0 g, crude). The crude material was taken to the next step without purification.

Provenance & Evidence