Hydrazine hydrate (1:1) → Azafluorene

Participants

Reaction Conditions

Reaction Steps

Indeno[2,1-b]pyridin-9-one (525 mg, 2.90 mmol), 92 (J. Org. Chem. 51, 2021 (1986)) and 4.5 mL of hydrazine hydrate were combined in a sealed tube and warmed to 180° C. for 16 hours. The resulting mixture was diluted with chloroform and the layers seperated. The organics were dried over sodium sulfate, filtered, and evaporated to dryness. The resulting oil was purified by chromatography on silica gel eluted with 95:5, 93:7, and 90:10 of methylene chloride:ethyl ether. The product fractions were evaporated to dryness to yield the title compound as a yellow solid.

Provenance & Evidence