4-Bromo-2-methylquinolin-3-ol → HCID 23078578, compound

HRID 228856Notes

Reaction equation

HRID 228856 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[C:3]=1[OH:13].Cl[C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][CH:16]=1>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[C:3]=1[O:13][C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 832554-Bromo-2-methylquinolin-3-olHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 23078578HCID 23078578, compoundYield 32%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
140 °C

Procedure

4-Bromo-3-hydroxy-2-methyl-quinoline (35 mg), 4-chloro-6,7-dimethoxyquinoline (110 mg), and 4-dimethylaminopyridine (89 mg) were suspended in o-dichlorobenzene (5 ml), and the suspension was stirred at 140° C. for 5 hr. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure. The residue was purified by thin layer chromatography using acetone-chloroform to give the title compound (20 mg, yield 32%).

Workup

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

Sources & evidence

ORD record
ord-67a5352e952a45119466a91766f94c83
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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