Triethylamine → 9-Ethyl-3-(hydrazinylidenemethyl)-9H-carbazole

Participants

Reaction Steps

A quantity of 98% hydrazine monohydrate (50 ml, 1.4 mole, obtained from Aldrich, Milwaukee, Wis.) and 10 ml of triethylamine (obtained from Aldrich, Milwaukee, Wis.) were added to a 250 ml, 2-neck round bottom flask equipped with a mechanical stirrer and an addition funnel. The solution was stirred vigorously at room temperature for a period of 10–15 min. A solution of 9-ethyl-3-carbazolecarboxaldehyde (22.3 g, 0.1 mol, obtained from Aldrich, Milwaukee, Wis.) in 30 ml of tetrahydrofuran (THF) was added slowly to the round bottom flask. After the addition of aldehyde was completed, the reaction mixture was stirred at room temperature for 2 hours. Then, the mixture was diluted with 50 ml of water. A precipitate was collected by filtration and washed repeatedly with water to give the crude 9-ethyl-3-carbazolecarboxaldehyde hydrazone, which was used in the next step immediately.

Provenance & Evidence