Sodium Hydroxide → X 9121

HRID 1648149Notes

Reaction equation

HRID 1648149 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[N:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[N:4]=[CH:3][CH:2]=1.Cl.[N:15]1[CH:20]=[CH:19][C:18]([CH2:21]Cl)=[CH:17][CH:16]=1.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1>[N:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:12]2([CH2:21][C:18]3[CH:19]=[CH:20][N:15]=[CH:16][CH:17]=3)[C:13]3[C:5](=[N:4][CH:3]=[CH:2][CH:1]=3)[C:6]3=[N:7][CH:8]=[CH:9][CH:10]=[C:11]23)=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 745704-(Chloromethyl)pyridinium chlorideHCID 11084280HCID 11084280, compound

Product 1

HCID 195376X 9121

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

The title compound was prepared following the procedure of Example 1 from 0.43 g (2.56 mmole) of 4,5-diazafluorene, 0.84 g of 4-picolylchloride hydrochloride, 29.0 mg of benzyltriethylammonium chloride, 3 ml of 50% sodium hydroxide, and 30 ml toluene by reaction at 50 for 6 hrs. The crude product was chromatographed (Ethylacetate/Methanol, 99:1) and recrystallized from isopropyl alcohol. NMR (CDCl3, 200 MHz) δ: 3.42(s,4H), 6.52(d,J=5.7 Hz,4H), 7.33(dd,2H), 7.85(d,2H), 8.16(d,J=5.6 Hz,4H), 8.61(d,2H).

Workup

  1. customby reaction at 50 for 6 hrs
  2. customThe crude product was chromatographed (Ethylacetate/Methanol, 99:1)
  3. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-5badf0293a344b7092f125abadc73f5b
Source dataset
uspto-grants-1995_07
Patent number
US05434264

Reaction notes

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