6-Hydroxyquinoline → 6,7-Dimethoxy-4-(6-quinolyloxy)quinoline

HRID 228536Notes

Reaction equation

HRID 228536 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[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[CH:22][CH:21]=[CH:20]2>>[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:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[CH:22][CH:21]=[CH:20]2

Participants

3

Reactant 2

HCID 113746-HydroxyquinolineHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 221326276,7-Dimethoxy-4-(6-quinolyloxy)quinolineYield 46.4%

Conditions

Temperature
180 °C

Procedure

A mixture of 4-chloro-6,7-dimethoxyquinoline (90 mg) with 6-hydroxyquinoline (176 mg) was stirred at 180° C. for 30 min. The reaction solution was cooled to room temperature, and was then purified by column chromatography on silica gel using acetone-hexane to give the title compound (62 mg, yield 46%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. customwas then purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a35b5a1a04ef473585ca0debf1347b3a
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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