3-Methoxy-10-nitro-6,11-dihydrodibenzo[b,e]thiepin-11-one → 10-Amino-3-methoxy-6,11-dihydrodibenzo[b,e]thiepin-11-one

Participants

Reaction Steps

In a mixture of water and ethanol (20 ml), 3-methoxy-10-nitro-6,11-dihydrodibenzo[b,e]thiepin-11-one obtained in Reference Example 18 (0.36 g, 1.2 mmol) was heated under reflux in the presence of reduced iron (0.36 g) and iron (III) chloride (40 mg) for 2 hours. After the reaction was completed, the reaction mixture was filtered while hot and the filtrate was evaporated under reduced pressure to give crude 10-amino-3-methoxy-6,11-dihydrodibenzo[b,e]thiepin-11-one (1.2 mmol). This crude product was added without purification to an acid chloride prepared from 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (0.38 g, 2.39 mmol) and thionyl chloride (0.36 ml, 2.39 mmol) in dimethylacetamide (10 ml) in the same manner as in Example 1-48, followed by stirring at room temperature for 6 hours. After the reaction, purification of the reaction product was carried out according to the procedure of Example 1-48 to give Compound 1-49 (0.32 g, yield: 65%).

Provenance & Evidence