Nitro Reduction

(Zn)

Examples:

Example 1

To a solution of the SM (130 mg, 0.2 mmol) in dioxane/H2O (3:1, 2 mL) was added NH4Cl (97 mg, 1.5 mmol) and Zn dust (80 mg, 1.5 mmol) at 0 C. The reaction mixture was stirred at RT for 3 h, after which time it was filtered through a celite bed. The filtrate was partitioned between H2O (10 mL) and EtOAc (30 mL). The org layer was separated, dried (Na2SO4), concentrated, and purified by column chromatography to provide the product as a yellow solid. [60 mg, 48%]

[Patent Reference: WO2014149164, page 211, (23.7 MB)]

Example 2

To a stirred solution of the SM (5 g, 25.25 mmol) in EtOH (60 mL) was added zinc powder (8.25 g, 126.26 mmol) and NH4Cl (6.8 g, 126.26 mmol). The resulting reaction mixture was stirred at 90 C for 6 h. The mixture was cooled to RT, filtered through a pad of celite, and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the product as a thick dark-brown solid. [2.5 g, 59%]

[Patent Reference: WO2014149164, page 387, (23.7 MB)]