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

HRID 457455Notes

Reaction equation

HRID 457455 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, 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.

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-22877fcf714e4e66a6230720a7d24e6a
Source dataset
uspto-grants-2007_03
Patent number
US07189482B2

Reaction notes

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