Title: Preparation of 4-amino-2,4-dioxobutanoic acid

Abstract

A process for synthesizing 4-amino-2,4-dioxobutanoate involves reacting a dialkyl oxalate with an alkoxide in ethanol to form a reaction mixture, and afterward adding an alkyl cyano acetate to the reaction mixture and allowing a reaction to proceed under conditions suitable to form a first reaction product of the formula diethyl 2-cyano-3-hydroxy-butenedioate, and then isolating the diethyl 2-cyano-3-hydroxy-butenedioate, and afterward reacting the diethyl-2-cyano-3-hydroxy-butenedioate with an aqueous hydroxide under conditions suitable to form 4-amino-2,4-dioxobutanoate. The 4-amino-2,4-dioxobutanoate may be acidified into 4-amino-2,4-dioxobutanoic acid.

Inventors:

Unkefer, Pat J.; Martinez, Rodolfo A.; Glass, David R.

Issue Date:

2016-03-22

Research Org.:

Los Alamos National Lab. (LANL), Los Alamos, NM (United States)

Sponsoring Org.:

USDOE

OSTI Identifier:

1243345

Patent Number(s):

9290443

Application Number:

14/489,329

Assignee:

Los Alamos National Security, LLC (Los Alamos, NM) New Mexico Highlands University (Las Vegas, NM)

Patent Classifications (CPCs):

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS

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C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C231/065 - {By hydration using metals or metallic ions as catalyst}
C07C253/30 - by reactions not involving the formation of cyano groups
C07C255/23 - containing cyano groups and carboxyl groups, other than cyano groups, bound to the same unsaturated acyclic carbon skeleton
C07C235/80 - having carbon atoms of carboxamide groups and keto groups bound to the same carbon atom, e.g. acetoacetamides

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DOE Contract Number:  

AC52-06NA25396

Resource Type:

Patent

Resource Relation:

Patent File Date: 2014 Sep 17

Country of Publication:

United States

Language:

English

Subject:

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 59 BASIC BIOLOGICAL SCIENCES