Hydrochloric Acid → HCID 86641294, compound

Participants

Reaction Steps

To a solution of nitroarene 26 (460 mg, 0.98 mmol) in MeOH (9 mL) was added saturated aqueous NH4Cl solution (3 mL) and zinc powder (319 mg, 4.88 mmol). 15 drops of aqueous 1N HCl were added and the reaction was stirred at room temperature for 18 h. EtOAc and saturated NaHCO3 aqueous solution were added and the mixture was filtered through celite. The filtrate was transferred into an extraction funnel and the layers were separated. The aqueous layer was extracted with EtOAc (2×). The combined organic layers were washed with saturated NaCl solution once, dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography on silica gel using a gradient of 0-5% MeOH in CH2Cl2 as eluant to provide aminobenzyl bisphosphonate 27 as a clear yellow oil (374 mg, 86%). 1H NMR (400 MHz, CDCl3) δ 2.69 (tt, J=24.0, 6.1 Hz, 1H), 3.18 (dt, J=16.7, 6.2 Hz, 2H), 4.46-4.60 (m, 8H), 5.19-5.22 (m, 4H), 5.29-5.35 (m, 4H), 5.84-5.94 (m, 4H), 6.60 (d, J=8.6 Hz, 2H), 7.06 (d, J=8.4 Hz, 2H).

Provenance & Evidence