Sulfuric Acid → 1,3,4,5-Tetrahydro-2H-1-benzazepin-2-one

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Reaction Conditions

Reaction Steps

A solution of sodium azide (25 g, 370 mmol) in water (13 mL) and chloroform (160 mL) is cooled to 0° C. and treated dropwise with concentrated sulfuric acid (11 mL). Stirring is continued for 30 min and the layers separated. The organic layer is dried over anhydrous sodium sulfate, filtered, and α-tetralone (20 g, 137 mmol) is added in one protion with stirring. The resulting solution is heated at 40° C. and concentrated sulfuric acid (38 mL) is added dropwise to maintain the internal temperature at 40-45° C. and stirring continued for 1 h, then cooled to 20° C. and poured into a sepratory funnel. The bottom layer is added dropwise with stirring to ise water (900 mL). The resulting solids are collected by filtration, and dried in vacuo at 40° C. to give 19.7 g of an off-white solid (89%), mp 139-140° C.; MS (ESI+) m/z 162 (M+H).

Provenance & Evidence