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

HRID 457457Notes

Reaction equation

HRID 457457 reaction equation
O.[NH2:2][NH2:3].C(N(CC)CC)C.[CH2:11]([N:13]1[C:25]2[CH:24]=[CH:23][C:22]([CH:26]=O)=[CH:21][C:20]=2[C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH3:12]>C1COCC1.O>[CH2:11]([N:13]1[C:25]2[CH:24]=[CH:23][C:22]([CH:26]=[N:2][NH2:3])=[CH:21][C:20]=2[C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH3:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 820559-ethyl-9H-carbazole-3-carbaldehyde

Product 1

HCID 674839059-Ethyl-3-(hydrazinylidenemethyl)-9H-carbazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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 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 THF was slowly added 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. The 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.

Workup

  1. customequipped with a mechanical stirrer and an addition funnel
  2. stirringthe reaction mixture was stirred at room temperature for 2 hours
  3. filtrationThe precipitate was collected by filtration
  4. washwashed repeatedly with water

Sources & evidence

ORD record
ord-cf33f31de40f45f58cb716337fedb058
Source dataset
uspto-grants-2007_03
Patent number
US07189482B2

Reaction notes

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