US 5,496,958 AGranted

Preparation of 5-vinylpyrrolidones

AssigneeBASF SE

InventorsRolf Fischer, Werner Hoffmann, Ernst Langguth, Hardo Siegel

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Abstract

A process for the preparation of a 5-vinylpyrrolidone of the formula ##STR1## wherein each of R.sup.1 and R.sup.2 is hydrogen or alkyl and R.sup.3 is preferably hydrogen but may further represent alkyl, cycloalkyl, aryl, alkylaryl, arylalkyl or a 5- to 6-membered aromatic or non-aromatic heterocyclic group containing 1 to 3 nitrogen atoms and/or an oxygen or sulfur atom, the process being carried out in two steps, first to react a 3-formylpropionic acid ester of the formula ##STR2## where each of R.sup.1 and R.sup.2 is hydrogen or C.sub.1 -C.sub.8 -alkyl, and R.sup.4 is hydrogen, alkyl, cycloalkyl, aryl, alkylaryl or arylalkyl, with a vinylymagnesium halide of the formula CH.sub.2 .dbd.CH--Mg--X V, where X is chlorine, bromine or iodine, at a temperature of from -30.degree. to 100.degree. C., under a pressure from 0.001 to 10 bar and in a molar ratio of V:IV of from 0.3:1 to 3:1 to obtain as an intermediate product a gamma-vinylbutyrolactone of the formula ##STR3## where R.sup.1 and R.sup.2 have the abovementioned meaning; and then reacting said intermediate of the formula II with ammonia or a primary amine of the formula R.sup.3 --NH.sub.2 III, where R.sup.3 has the abovementioned meaning, at a temperature of from 150.degree. to 350.degree. C. and under a pressure of from 0.1 to 200 bar.

Claims6

Dependent claims

A process for the preparation of a 5-vinylpyrrolidone of the formula ##STR7## wherein each of R.sup.1 and R.sup.2 is hydrogen or C.sub.1 -C.sub.8 -alkyl, and R.sup.3 is a substituent selected from the group consisting of hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, aryl, C.sub.7 -C.sub.12 -alkylaryl and C.sub.7 -C.sub.12 -arylalkyl,

said process comprising:
firstreacting a 3-formylpropionic acid ester of the formula ##STR8## where each of R.sup.1 and R.sup.2 is hydrogen or C.sub.1 -C.sub.8 -alkyl, and R.sup.4 is a substituent selected from the group consisting of hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, aryl, C.sub.7 -C.sub.12 -alkylaryl and C.sub.7 -C.sub.12 -arylalkyl,
with a vinylymagnesium halide of the formula
CH.sub.2 .dbd.CH--Mg--X V,
where X is chlorine, bromine or iodine, at a temperature of from -30.degree. to 100.degree. C., under a pressure from 0.001 to 10 bar and in a molar ratio of V:IV of from 0.3:1 to 3:1 to obtain as an intermediate product a gamma-vinylbutyrolactone of the formula ##STR9## where R.sup.1 and R.sup.2 have the abovementioned meaning;
and then reacting said intermediate of the formula II with ammonia or a primary amine of the formula
R.sup.3 --NH.sub.2 III,
where R.sup.3 has the abovementioned meaning, at a temperature of from 150.degree. to 350.degree. C. and under a pressure of from 0.1 to 200 bar.

5 more elements

Dependencies are inferred from the claim text.