Sodium hydride → 2-Methoxyquinolin-8-amine

Participants

Reaction Steps

Thus, the 8-amino-2-chloroquinoline VI was allowed to react with a solution of sodium methylate in DMF (prepared under nitrogen by adding sodium hydride to a solution of methanol in DMF accompanied by the liberation of hydrogen). This procedure afforded 8-amino-2-methoxyquinoline VII. The introduction of the 8-(4-amino-1-methylbutyl) side chain was accomplished in the same manner as for the COMPARATIVE COMPOUND (U.S. Pat. No. 4,431,801). Thus intermediate VII was treated with 4-iodo-1-phthalimidopentane to give the target precursor 8-(4-phthalimido-1-methylbutylamino)quinoline VIII. The phthalimido group was removed with hydrazine to give the title compound free base IX. The free base was treated with succinic acid in a suitable solvent system to give the 2-methoxy target compound X as the succinic acid salt.

Provenance & Evidence