Sodium Hydroxide → 9,9-Bis(4-pyridinylmethyl)-2-fluorofluorene dihydrochloride

HRID 1463672Notes

Reaction equation

HRID 1463672 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[ClH:15].[N:16]1[CH:21]=[CH:20][C:19]([CH2:22][Cl:23])=[CH:18][CH:17]=1.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1>[ClH:23].[ClH:15].[N:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:5]2([CH2:22][C:19]3[CH:20]=[CH:21][N:16]=[CH:17][CH:18]=3)[C:4]3[CH:3]=[C:2]([F:1])[CH:14]=[CH:13][C:12]=3[C:11]3[C:6]2=[CH:7][CH:8]=[CH:9][CH:10]=3)=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 745704-(Chloromethyl)pyridinium chlorideHCID 2411322-Fluorofluorene

Product 1

HCID 190904979,9-Bis(4-pyridinylmethyl)-2-fluorofluorene dihydrochloride

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

The title compound was prepared following the method of Example 1 from 4.0 g (21.74 mmole) of 2-fluorofluorene, 8.92 g of 4-picolylchloride hydrochloride, 120 ml of toluene, 200 mg of benzyltriethylammonium chloride, and 20 ml of 50% sodium hydroxide by reaction at 22° for 17 hrs. The product was chromatographed (silica, CH2Cl2 /MeOH, 10:1) to yield 2.9 g which was recrystallized (ethanol-acetone) and converted to the dihydrochloride, m.p. >300°.

Workup

  1. customby reaction at 22° for 17 hrs
  2. customThe product was chromatographed (silica, CH2Cl2 /MeOH, 10:1)
  3. customto yield 2.9 g which
  4. customwas recrystallized (ethanol-acetone)

Sources & evidence

ORD record
ord-d3b94428d93846a6b30aeb024e38248a
Source dataset
uspto-grants-1994_04
Patent number
US05300642

Reaction notes

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