5-Chloro-2-hydroxybenzamide → 5-Chloro-2-[(6,7-dimethoxy-4-quinolyl)oxy]benzamide

HRID 228638

Reaction equation

HRID 228638 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.[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([OH:26])=[C:21]([CH:25]=1)[C:22]([NH2:24])=[O:23]>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([O:26][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][CH:3]=2)=[C:21]([CH:25]=1)[C:22]([NH2:24])=[O:23]

Participants

5

Reactant 2

HCID 3480945-Chloro-2-hydroxybenzamideHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 577563635-Chloro-2-[(6,7-dimethoxy-4-quinolyl)oxy]benzamideYield 165.2%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (100 mg), 5-chloro-2-hydroxybenzamide (343 mg), and 4-dimethylaminopyridine (244 mg) were suspended in o-dichlorobenzene (1 ml), and the suspension was stirred at 120° C. overnight. The reaction solution was cooled to room temperature, and the solvent was removed therefrom by distillation under the reduced pressure. The residue was purified by column chromatography using acetone-hexane to give the title compound (265 mg, yield 100%).

Workup

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

Sources & evidence

ORD record
ord-6953a73f3758450097841db38d2bbb6c
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Linked notes

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