Acetic Acid → [(9-Ethyl-9h-carbazol-3-yl)methylene]malononitrile

HRID 435558Notes

Reaction equation

HRID 435558 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([CH:16]=O)=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].[C:18](#[N:22])[CH2:19][C:20]#[N:21].C(O)(=O)C.C([O-])(=O)C.[NH4+]>C1C=CC=CC=1>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([CH:16]=[C:19]([C:18]#[N:22])[C:20]#[N:21])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8010MalononitrileHCID 820559-ethyl-9H-carbazole-3-carbaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 290167[(9-Ethyl-9h-carbazol-3-yl)methylene]malononitrile

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

About 11.1 grams (0.05 moles) N-ethyl carbazole-3-carboxaldehyde, about 3.1 grams (0.05 moles) malononitrile, about 1 milliliter glacial acetic acid, about 0.35 grams ammonium acetate and about 40 milliliters benzene are heated to boiling under reflux conditions for about 30 minutes. The liquid portion of this mixture is separated from the brown colored solution by rotary evaporation, the solid residues twice recrystallized with glacial acetic acid washed with ethanol and dried in a vacuum oven. Yield: 7.0 grams of bright yellow needle like crystals m.p. 164°-165° C.

Workup

  1. customThe liquid portion of this mixture is separated from the brown colored solution by rotary evaporation
  2. customthe solid residues twice recrystallized with glacial acetic acid
  3. washwashed with ethanol
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-48f2385810d848cb81c381b97afbe48f
Source dataset
uspto-grants-1977_02
Patent number
US04006017

Reaction notes

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