Hydrochloric Acid → HCID 10687015, compound

Participants

Reaction Steps

Nitromethane (1.22 g, 0.02 mol) was added to an ice-cooled mixture of 2-(methanesulfonylamino)-5-(methoxycarbonyl)benzaldehyde (2.57 g, 0.01 mol) in ethanol and the mixture stirred for 10 min. To this mixture was added potassium hydroxide (1.23 g, 0.022 mol in 20 mL 90% ethanol) at 0° C. over a period of 20 min. The reaction mixture was further stirred at 0° C. for 0.5 h and then at room temperature for 4 h. The mixture was neutralized with 2N HCl and poured in water (100 mL). The mixture was extracted with chloroform, dried over sodium sulfate, filtered, and concentrated. The residue was passed through a column of silica gel eluting with chloroform:methanol (99:1 to 95:5). The desired pure fractions were combined, concentrated, recrystallized from ethyl acetate-hexane, and dried to give 0.8 g (25%) of methyl 3-[1-(R,S)-hydroxy-2-nitroethyl]-4-[(methylsulfonyl)amino]benzoate as off-white crystals, mp 148° C.

Provenance & Evidence