Acetic Acid → 9H-Fluorene-2-carbonitrile

HRID 1678372Notes

Reaction equation

HRID 1678372 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[CH:14]=O.C([O-])(=O)C.[Na+].[Cl-].O[NH3+:23].C(O)(=O)C>O>[C:14]([C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:12][C:13]=2[CH:1]=1)#[N:23]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 21645Hydroxylamine HClHCID 34804Fluorene-2-carboxaldehydeHCID 517045Sodium Acetate

Product 1

HCID 173029H-Fluorene-2-carbonitrileYield 63.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

25 g of 2-fluorenecarboaldehyde, 11.6 g of sodium acetate, 9.7 g of hydroxy ammonium chloride and 150 ml of acetic acid were stirred at 130 for 18 hours. The reaction mixture was allowed to room temperature, poured into 200 ml of water and the precipitate was collected by filtration. The crude product was purified by column chromatography, giving 15.57 g (63%) of 2-cyanofluorene.

Workup

  1. customwas allowed to room temperature
  2. filtrationthe precipitate was collected by filtration
  3. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-c38194389ac749a1a244c711695c52a3
Source dataset
uspto-grants-2011_08
Patent number
US08008507B2

Reaction notes

Loading…