Ammonium Chloride → HCID 131736621, compound

Participants

Reaction Conditions

Reaction Steps

To the solution of 24B (0.33 g, 0.772 mmol) in MeOH (7.72 ml) was added ammonium chloride (0.413 g, 7.72 mmol) and zinc (0.505 g, 7.72 mmol). The reaction was stirred at 55° C. for 5 h. The reaction was cooled to rt, filtered, and the filtrate was concentrated. The residue was partitioned between EtOAc and sat. NaHCO3 and the layers were separated. The organic layer was washed with water, brine, dried over Na2SO4, filtered, and concentrated to afford the aniline (0.317 g, 103%) as a yellow solid. MS (ESI) m/z: 398.2 (M+H)+. To a cooled (−78° C.) clear solution of the aniline (0.317 g, 0.798 mmol) and pyridine (0.097 ml, 1.196 mmol) in DCM (7.98 ml) was added dropwise methyl chlorocarbonate (0.074 ml, 0.957 mmol). The reaction was stirred at −78° C. for 1 h, the reaction was quenched with sat. NH4Cl and the reaction was allowed to warm to RT. The reaction was diluted with DCM and water and the layers were separated. The aqueous layer was extracted with DCM (1×). The combined organic layers were washed with sat. NaHCO3, brine, dried over Na2SO4, filtered and concentrated to give a brown foam. Purification by normal phase chromatography provided 24C (0.304 g, 84%) as a white solid. MS (ESI) m/z: 456.2 (M+H)+.

Provenance & Evidence