Methyl iodide → 3-Methoxyquinoline

HRID 863280

Reaction equation

HRID 863280 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.[OH:9][C:10]1[CH:11]=[N:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2>CN(C)C=O.C(OCC)C>[CH3:1][O:9][C:10]1[CH:11]=[N:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 113763-HydroxyquinolineHCID 11430Potassium Carbonate

Product 1

HCID 5758073-Methoxyquinoline

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

1.05 g of anhydrous potassium carbonate and 0.48 ml of methyliodide are added to a solution of 1.0 g of 3-hydroxyquinoline in 8.5 ml of dimethylformamide and the reaction mixture is stirred at room temperature for 18 h. It is diluted with diethyl ether, the resulting suspension is filtered and the filtrate is concentrated. The crude product is purified by FC over 60 g of silica gel (mobile phase F) to give 3-methoxyquinoline: Rf (A)=0.53.

Workup

  1. filtrationthe resulting suspension is filtered
  2. concentrationthe filtrate is concentrated
  3. customThe crude product is purified by FC over 60 g of silica gel (mobile phase F)

Sources & evidence

ORD record
ord-8ee420d42c2148ab89a0b94ec8ce8b40
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Linked notes

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