Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1) → 4,6-Dichloro-1,2-dimethylquinolinium tetrafluoroborate

HRID 2118596Notes

Reaction equation

HRID 2118596 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[F:14][B-:15]([F:18])([F:17])[F:16].[CH3:19][O+](C)C>C(#N)C>[F:14][B-:15]([F:18])([F:17])[F:16].[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[N+:5]([CH3:19])=[C:4]([CH3:13])[CH:3]=1

Participants

4

Reactant 2

HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 123225774,6-Dichloro-2-methylquinoline

Product 1

HCID 200290004,6-Dichloro-1,2-dimethylquinolinium tetrafluoroborateYield 78.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The starting material may be prepared as follows. Powdered 4,6-dichloro-2-methylquinoline (254 mg.) was added to a stirred solution of trimethyloxonium tetrafluoroborate (177 mg.) in acetonitrile (1 ml.), and stirring was continued overnight. The solvent was evaporated and the residue was triturated with ether to give 4,6-dichloro-1,2-dimethylquinolinium tetrafluoroborate (296 mg.). N.m.r. in solvent A: 3.07(s, 3H); 4.44(s, 3H); 7.9-8.8(complex, 4H).

Workup

  1. customThe starting material may be prepared
  2. customThe solvent was evaporated
  3. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-5ad3f30b3de1403aa8cd019171bb9eb5
Source dataset
uspto-grants-1987_07
Patent number
US04678781

Reaction notes

Loading…