Ammonium Chloride → HCID 21959409, compound

Participants

Reaction Steps

4-(2-tert-Butyl-5-nitrophenyl)-1-methylpyridinium (2.1 g, 7.8 mmol) (Step C) was added to a 100 mL round-bottom flask and dissolved in a 10% H2O/EtOH mixture. Iron dust (1.31 g, 23.4 mmol, 3 eq) and NH4Cl (460 mg, 8.6 mmol, 1.1 eq) were added. The flask was heated to reflux. After 2 h, the solution was cooled to RT and filtered through a pad of Celite®. The resulting solution was stripped down to a yellow solid and redissolved in MeOH (20 mL, anhydrous). The solution was cooled to 0° C. and slowly adding NaBH4 (450 mg, 11.7 mmol, 1.5 eq). The solution was cooled to RT and stirred for 30 min. The solvent was stripped-off under vacuum and the solid was redissolved in CH2Cl2 and filtered. The solution was concentrated in vacuo to afford an amorphous clear yellow solid. MS (ES+): 245.2 (M+H)+

Provenance & Evidence