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

HRID 268575

Reaction equation

HRID 268575 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]>O1CCCC1.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 a period of 10-15 min. A solution of 9-ethyl-3-carbazolecarboxaldehyde (22.3 g, 0.1 mol, from Aldrich, Milwaukee, Wis.) in 30 ml of tetrahydrofuran (THF) were 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. Next, the reaction mixture was diluted with 50 ml of water. A precipitate was collected by filtration and washed repeatedly with water to give 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. filtrationA precipitate was collected by filtration
  4. washwashed repeatedly with water

Sources & evidence

ORD record
ord-e024a7e79af74dc399a5e20191e6eeff
Source dataset
uspto-grants-2008_11
Patent number
US07445877B2

Linked notes

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