Hydrochloric Acid → 9,9-Bis(4-pyridinylmethyl)-2-methoxyfluorene dihydrochloride

HRID 1463675Notes

Reaction equation

HRID 1463675 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6][C:5]=2[CH:4]=1.[N:16]1[CH:21]=[CH:20][C:19]([CH2:22][Cl:23])=[CH:18][CH:17]=1.[ClH:24].[OH-].[Na+]>C1(C)C=CC=CC=1>[ClH:23].[ClH:24].[N:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:6]2([CH2:22][C:19]3[CH:20]=[CH:21][N:16]=[CH:17][CH:18]=3)[C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:15]=[CH:14][C:13]=3[C:12]3[C:7]2=[CH:8][CH:9]=[CH:10][CH:11]=3)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 173012-MethoxyfluoreneHCID 745714-(Chloromethyl)pyridine

Product 1

HCID 190904999,9-Bis(4-pyridinylmethyl)-2-methoxyfluorene dihydrochloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared following the procedure of Example 5 from 1.8 g (9.2 mmole) of 2-methoxyfluorene, 3.0 g of 4-picolylchloride.HCl, 20 ml of 50% NaOH, 100 mg of cetyl Bu3PBr, and 30 ml of toluene by reaction at 50° for 6 hrs. The material was chramato-graphed to yield 1.6 g of product. δ: 3.37(s,4H), 3.89(s,3H), 6.52(broad,4H), 6.80(m,1H), 7.01(d,J=2.1 Hz,1H), 7.26(m,5H), 7.45(d,J=7.5 Hz,1H), 8.11(broad,4H).

Sources & evidence

ORD record
ord-a9131d15b38c4e039f30bb61afa22834
Source dataset
uspto-grants-1994_04
Patent number
US05300642

Reaction notes

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