Cl[Sn]Cl.Cl.[CH3:5][C:6]1[C:14]2[S:13][CH:12]=[N:11][C:10]=2[CH:9]=[CH:8][C:7]=1[N+:15]([O-])=O.[OH-].[Na+]>>[CH3:5][C:6]1[C:14]2[S:13][CH:12]=[N:11][C:10]=2[CH:9]=[CH:8][C:7]=1[NH2:15]To a solution of SnCl2 (3.0 g, 3.8 mmol) and 10 mL of con.HCl was added 7-methyl-6-nitrobenzothiazole (0.68 g, 3.5 mmol) in a portion and the resulting reaction mixture was stirred for 1 h at 25° C. The reaction mixture was basified with aqueous NaOH and extracted with EtOAc and CHCl3. Combined organic layers were dried over Na2SO4 and concentrated in vacuo, yielding an oil (0.65 g, >95%) which was identified as the desired amine and subjected to a following reaction without further purification.
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