Hydrochloric Acid → HCID 5115807, compound

Participants

Reaction Steps

A 80 mL Fischer-Porter® bottle (Fischer-Porter Co., Warminster, Pa.) equipped with a gas pressure head and a magnetic stirring bar was charged with methyl 4-methoxy-2-nitrophenyl-α-cyano-acetate from Example 10 (5.0 g, 0.020 mol), methanol (3 mL), toluene (50 mL), sealed, and then charged with HCl gas (55 psig). After stirring for 4 hours at ambient temperature, the apparatus was vented and water (50 mL) was added. The toluene layer was separated and evaporated to dryness under vacuum to afford 5.1 g of dimethyl 4-methoxy-2-nitrophenylmalonate as a tan colored solid (1H-NMR). By HPLC area % analysis (254 nm), the solid was 95% dimethyl 4-methoxy-2-nitrophenylmalonate and 5% methyl 4-methoxy-2-nitrophenyl-α-carbamido-acetate. Isolated yield: 86% on methyl 4-methoxy-2-nitrophenyl-α-cyanoacetate.

Provenance & Evidence