4-Chloro-6,7-dimethoxyquinoline → HCID 23156507, compound

HRID 228792Notes

Reaction equation

HRID 228792 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][C:4]([C:8]2[C:13]([OH:14])=[CH:12][CH:11]=[C:10]([CH3:15])[N:9]=2)=[N:3]1.Cl[C:17]1[C:26]2[C:21](=[CH:22][C:23]([O:29][CH3:30])=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][CH:18]=1>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][C:4]([C:8]2[C:13]([O:14][C:17]3[C:26]4[C:21](=[CH:22][C:23]([O:29][CH3:30])=[C:24]([O:27][CH3:28])[CH:25]=4)[N:20]=[CH:19][CH:18]=3)=[CH:12][CH:11]=[C:10]([CH3:15])[N:9]=2)=[N:3]1

Participants

5

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 135854833HCID 135854833, compound

Product 1

HCID 23156507HCID 23156507, compoundYield 4.2%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
160 °C

Procedure

2-(1,5-Dimethyl-1H-pyrazol-3-yl)-6-methyl-pyridin-3-ol (111 mg), 4-chloro-6,7-dimethoxyquinoline (218 mg), and 4-dimethylaminopyridine (130 mg) were suspended in o-dichlorobenzene (5 ml), and the suspension was stirred at 160° C. for 2 days. The reaction solution was cooled to room temperature, and the solvent was then removed by distillation under the reduced pressure. The residue was purified by thin layer chromatography using methanol-chloroform to give the title compound (9 mg, yield 4%).

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 thin layer chromatography

Sources & evidence

ORD record
ord-7ea66de1a06344ab9065bef501a745c0
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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