Hydrochloric Acid → 2-Amino-1(2H)-isoquinolinone

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Reaction Steps

A solution of isocoumarin (26 g, 0.16 mol) in 95% ethanol (2000 ml) was treated with 25% hydrazine hydrate in water (64 ml, 0.32 mol) and stirred at room temperature for one hour. The precipitate of 2-amino-3,4-dihydro-3-hydroxy-1H(2H)-isoquinolinone was dissolved and dehydrated by addition of 10% hydrochloric acid (150 ml) at room temperature. After three hours, the mixture was neutralized with sodium carbonate and the ethanol recovered by distillation in vacuo. The title compound was isolated by filtration and extraction with chloroform to give 27.92 g (98%) of the product of the title. M.p. 103°-4° C.

Provenance & Evidence