Hydrochloric Acid → HCID 86729934, compound

Participants

Reaction Steps

In a 100-mL three-neck flask were put 0.53 g (2.5 mmol) of 4-chlorobenzo[h]quinazoline, 52 mg (0.148 mmol) of tris(2,4-pentanedionato)iron(III) (abbreviation: Fe(acac)3), 25 mL of dehydrated tetrahydrofuran (THF), and 2.0 mL of 1-methyl-2-pyrrolidone (abbreviation: NMP), and the air in the flask was replaced with nitrogen. The flask was cooled with ice, 2.6 mL of isobutylmagnesium bromide solution (1 M in THF) (abbreviation: iBuMgBr) was added, and the mixture was stirred at room temperature for 16 hours. Then, 1 M hydrochloric acid was added, and an organic layer was subjected to extraction with ethyl acetate. The solution of the extract was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. After washing, anhydrous magnesium sulfate was added to the organic layer for drying. The resulting mixture was subjected to gravity filtration, and the filtrate was concentrated to give a residue. The residue was purified by silica gel column chromatography. As the developing solvent, first, dichloromethane was used; then, a 10:1 dichloromethane-ethyl acetate mixed solvent was used. The resulting fraction was concentrated to give 0.14 g of an orange oily substance in a yield of 24%. Synthesis Scheme (b-1) of Step 1 is shown below.

Provenance & Evidence