Dimethylformamide → HCID 21897597, compound

Participants

Reaction Steps

For example, aryl-[(aminoalkoxy)-aryl]methanone oxime hydrochloride of structure 7 can be stirred in a suitable protic solvent such as isopropyl alcohol, methanol, ethanol or 2-methoxymethanol, any of which may be mixed with water. The mixture is treated with an appropriate base such as 45% potassium hydroxide solution or potassium carbonate with catalytic copper powder. Alternatively, the oxime of structure 7 can be stirred with an anhydrous solvent such as dimethylformamide or N-methylpyrrolidine under nitrogen. The mixture is treated with an appropriate base such as sodium hydride or potassium t-butoxide with catalytic copper powder. The reaction is held at a temperature from 40° C. to approximately 80° C., for a period of 4 hours to overnight. The mixture can be cooled and filtered, and the crude product isolated and purified by methods known to one skilled in the art, to give the appropriate substituted benzisoxazole or pyridylisoxazole of compound 1(f).

Provenance & Evidence