2,3-Dihydroxybutanedioic Acid → HCID 70363399, compound

Participants

Reaction Steps

A mixture of 32.4 g. (0.10 moles) of 2-chloro-12-(3-chloropropyl)-12H-dibenzo[d,g][1,3,6]dioxazocine prepared by the method of Example 1, 11.8 g. (0.20 moles) of isopropyl amine, 7.5 g. of sodium iodide and 200 ml. of methyl ethyl ketone is stirred under reflux for 20 hours. Thereafter the solvent is removed in vacuo, 100 ml. of benzene are added to the residue and the mixture obtained is washed with water. Thereafter 37.5 g. (0.25 moles) of tartaric acid and 150 ml. of water are added to the organic phase and the reaction mixture is stirred for 30 minutes. The aqueous phase is separated, 150 ml. of methylene chloride are added thereto and the pH is adjusted to 10 by using aqueous ammonia. The organic phase is separated and the solvent is removed. The residue is dissolved in 100 ml. of isopropanol and a solution of 9.5 g (0.82 moles) of maleic acid is added thereto. The precipitated white product is filtered off, dried and recrystallized from isopropanol. There are obtained 32.4 g. (70.0%) of the title product, melting at 126° to 129° C.

Provenance & Evidence