Water → HCID 53825779, compound

Participants

Reaction Steps

NaH (60% dispersion in mineral oil, 0.23 g, 12.0 mmol) was washed (2×) with hexanes then suspended in THF (10 mL) to which 2-hydroxymethyl-α-methyoxyimino-N-methyl-benzeneacetamide (0.89 g, 4.0 mmol) in THF solution was added. The solution was stirred at room temperature for 10 minutes at which time isopropyl-5,6-dichloronicotinate (1.00 g, 4.3 mmol) in THF solution was added. After 15 minutes of stirring at room temperature, the solution was poured into 4-5 volumes of water and extracted with Et2O (2×100 mL) . The organics were dried over MgSO4 and concentrated to 1.5 g tan, viscous oil. Crude product was chromatographed using silica gel (230-400 mesh) with descending solvent gradient from 100% petroleum ether to 80/20 petroleum ether/ethyl acetate as the mobile phase. Elution and concentration gave α-(methoxyimino)-N-methyl-2-[[[3-chloro-5-(isopropoxycarbonyl)-2-pyridinyl]oxy]methyl]-benzeneacetamide (0.72 g) as a white solid.

Provenance & Evidence