Reacción #43304

Ecuación de reacción

6-(4-methyl-3-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole

tin(II) chloride

sodium hydroxide

→

title compound

Rendimiento 28.0%

6-(3-Amino-4-methylphenyl)-3-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole

Rendimiento 28.0%

Disolventes

methanol

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas refluxed under argon for 6 h
2. 2
   Extracciónextracted with ethyl acetate (3×20 mL)
3. 3
   OtroThe extracts were dried
4. 4
   Concentraciónconcentrated
5. 5
   Otrothe residue was purified by column chromatography (EtOAc as eluent)

Procedimiento

A mixture of 6-(4-methyl-3-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole (256 mg, 0.6 mmol) and tin(II) chloride (675 mg, 3 mmol) in methanol (25 mL) was refluxed under argon for 6 h. It was then diluted with water (30 mL) and neutralized with 2N aqueous sodium hydroxide to pH=12, and extracted with ethyl acetate (3×20 mL). The extracts were dried, concentrated and the residue was purified by column chromatography (EtOAc as eluent) to give 66 mg (28%) of the title compound as solid. 1H NMR (CDCl3): 7.71 (s, 2H), 7.23 (m, 2H), 7.17 (s, 1H), 4.00 (s, 6H), 3.94 (s, 3H), 2.26 (s, 3H).

Fuente