2-Amino-3-chloro-1,4-naphthoquinone → HCID 15345814, compound

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Reaction Steps

To a solution of 5.00 g (24 mmol) of 2-amino-3-chloro-1,4-dihydro-1,4-dioxonaphthalene in 37 mL (280 mmol) of 2-methylbenzoic acid chloride, 8 drops of concentrated sulfuric acid are added with protection from light. After 7 h of reflux and complete cooling, the ocher precipitate that forms is filtered through fritted glass, washed with ether, and purified on a flash column (support: silica; conditioning: heptane; eluant: dichloromethane/heptane, 50/50). The yellow powder obtained after evaporation of the solvent is uncolored, and recrystallized in dichloromethane to produce 2.34 g of 4,9-dihydro-4,9-dioxo-2-(2-methylphenyl)-naphtho[2,3-d]oxazole in the form of yellow crystals.

Provenance & Evidence