Diethyl Malonate → Acetamidomalonic acid diethyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,4-dioxane, acetic acid and water, obtained from a previous reaction mixture by taking a low-boiling cut, was metered into a stirred mixture of 320.4 g (2.0 mol) of diethyl malonate and 160 g (2.3 mol) of sodium nitrite (technical grade), maintained at 35° C. 12.0 g of water were then metered in and 166 g (207. mol) of acetic acid (96%) were added dropwise over 2 hours. The mixture was allowed to continue reacting for 2 hours at 40° C. and was worked up as described in Example 4. There remained 425 g of light yellow oil, which, after catalytic hydrogenation and recrystallization of the crude product, gave diethyl acetaminomalonate at a yield of 86% of theory, based on the diethyl malonate employed, and with a purity of >99.8 FID area percent.

Provenance & Evidence