Sodium hydride → Methyl 3-[4-(3-chlorophenyl)-1-ethyl-7-formyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoate

Participants

Reaction Steps

In DMF was treated 3-(3-chlorobenzoyl)-2-ethylamino-6-dimethoxymethylpyridine with 60% sodium hydride, followed by the reaction with monoethyl chloroglutarate. Thereafter, the reaction mixture was worked up and purified in a usual manner. The resulting compound was reacted in ethanol in the presence of sodium methoxide under heating, and the reaction mixture was worked up and purified in a usual manner. Then, the resulting compound was reacted in a solution of 6M hydrochloric acid-dioxane (1:1) under heating, and then the reaction mixture was worked up and purified in a usual manner. The resulting compound was further reacted with methyl iodide in DMF in the presence of potassium carbonate, and then the reaction mixture was worked up and purified in a usual manner to obtain methyl 3-[4-(3-chlorophenyl)-1-ethyl-7-formyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoate. NMR1: 10.11 (1H, d, J=0.6 Hz), 2.45-2.95 (4H, m), 1.43 (3H, t, J=7.1 Hz).

Provenance & Evidence