2-Amino-6-chlorobenzoic acid → HCID 67740431, compound

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Reaction Steps

18.01 g 6-chloroanthranilic acid suspended in 100 mL toluene was treated with 14 mL 1-aza-2-methoxy-1-cycloheptene (1) and refluxed with stirring under a Dean-Stark trap to remove the forming water and methanol for 1 hour. An exothermic reaction ensued, forming a two-layer mixture and foaming considerably. This gradually dissolved, giving a brown solution. Then 9 mL of (1) was added and the mixture was refluxed for 18 more hours. The toluene was removed in vacuo and excess of (1) was distilled out at 11 mmHg at 140° C. bath. The residue was chromatographed (6:1 chloroform-ethyl acetate) and recrystallized from hexane-ethyl acetate. The product, 1-chloro-tetrahydroazepino[2,1-b]quinazolin-12(6H)-one, was obtained as a white, crystalline solid, m.p. 128° C.-129° C.; yield 16.5 g.

Provenance & Evidence