Water → HCID 53949472, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60%, 0.12 g, 3.0 mmol) was added to a solution of 3-chloro-2-hydroxymethyl-α-methyoxyimino-N-methyl-benzeneacetamide (0.43 g, 1.68 mmol) in dry THF (10 mL) and stirred for 10 minutes at 25° C. under N2 atmosphere. 5,6-Dichloronicotinic acid; t-butyl ester (0.44 g, 1.87 mmol) in 2-3 mL THF was added to this reaction mixture and stirred at 25° C. for about two hours. Water (40 mL) was added and the resulting mixture was extracted with ether (2×), dried (anhydrous Na2SO4), filtered and concentrated in vacuo to yield 0.72 g crude oil. The oil was chromatographed with dry pack silica gel (230-400 mesh) with descending solvent gradient from 100% petroleum ether to 80/20 pet ether/ethyl acetate as mobile phase. Elution and concentration gave α-(methoxyimino)-N-methyl-2-[[[3-chloro-5-(t-butoxycarbonyl)-2-pyridinyl]oxy]methyl]-3-chloro-benzeneacetamide (430 mg) as an oil. (95% E isomer; 5% Z isomer).

Provenance & Evidence