Hydrochloric Acid → 1-(2-amino-4-chlorophenyl)-2-(1-methyl-1-H-tetrazol-5-yl)ethanone

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Reaction Steps

A solution of butyl lithium in hexane (1.6M, 20.8 ml) was added slowly to a stirred mixture of 1,5-dimethyltetrazole (3.26 g) and dry tetrahydrofuran (70 ml) at 0° under nitrogen. The mixture was stirred at 0° for 0.5 hour and then 7-chloro-1H-3,1-benzoxazine-2,4-dione (2.17 g) was added in portions at 0° to 5°. The mixture was stirred at room temperature for 3 hours, then poured into water (200 ml) and acidified with 5N hydrochloric acid to pH 6 to 7. The mixture was extracted with dichloromethane (4×70 ml). The extracts were combined, dried over anhydrous magnesium sulphate and evaporated to give the novel compound 1-(2-amino-4-chlorophenyl)-2-(1-methyl-1-H-tetrazol-5-yl)ethanone as an oil that was used in the next stage without purification.

Provenance & Evidence