4-Chloro-6,7-dimethoxyquinoline → HCID 178486809, compound

HRID 228737Notes

Reaction equation

HRID 228737 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[OH:16][C:17]1[C:22]([OH:23])=[CH:21][CH:20]=[CH:19][N:18]=1>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[O:23][C:22]1[C:17]([OH:16])=[N:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 178516237HCID 178516237, compound

Product 1

HCID 178486809HCID 178486809, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
160 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (252 mg), 2,3-dihydroxypyridine (396 mg), and 4-dimethylaminopyridine (400 mg) were suspended in o-dichlorobenzene (13 ml), and the suspension was stirred at 160° C. overnight. The reaction solution was cooled to room temperature, the solvent was then removed by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-chloroform to give 6,7-dimethoxy-4-(2-hydroxy-pyridin-3-yloxy)-quinoline (84 mg, yield 25%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. customthe solvent was then removed by distillation under the reduced pressure
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-0f8dfd47f7934b4592296b1d5fabb679
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

Loading…