Substituted quinoline herbicide intermediates and process
AssigneeAmerican Cyanamid Company
InventorWen-Xue Wu
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Abstract
The invention is substituted quinoline intermediates useful in the synthesis of the herbicide 2-(4-isopropyl-4-methyl 5-oxo 2-imidazolidinyl)-5-methoxymethylnicotinic acid and a process for preparing the herbicide intermediate 3-methoxymethyl-7- or 8-hydroxyquinoline.
Claims15
A compound of the formula ##STR12## wherein X is straight or branched C.sub.1 -C.sub.6 alkyl, phenyl, --O--C.sub.1 -C.sub.4 straight or branched alkyl ##STR13## wherein Y and z are independently H, straight or branched C.sub.1 -C.sub.6 alkyl or phenyl and
- B is halogen, or a quaternary ammonium halide.
A compound of the formula ##STR14## wherein B is a quaternary ammonium halide.
A process for preparing a compound of the formula ##STR15## which comprises reacting a compound of the formula ##STR16## wherein X is straight or branched C.sub.1 -C.sub.6 alkyl, phenyl, --O--C.sub.1 -C.sub.4 straight or branched alkyl or ##STR17## wherein Y and Z are independently H, straight or branched C.sub.1 -C.sub.6 alkyl or phenyl with a radical halogenating reagent wherein the halogen is bromine or chlorine to form a compound of the formula ##STR18## reacting compound III with a tertiary amine without a reactive beta-hydrogen to form a compound of the formula ##STR19## wherein B is a quaternary ammonium halide;
- and reacting compound IV with a base in methanol at a temperature within the range of about 120.degree. to about 180.degree. C. in a closed reactor to form a compound of formula I;
- or
- reacting compound IV with a base in methanol in the presence of a transition metal salt at a temperature within the range of about 65.degree. C. to about 180.degree. C. in a closed reactor to form a compound of formula I.
Dependencies are inferred from the claim text.