4-Chloro-6,7-dimethoxyquinoline → 3-(6,7-Dimethoxy-quinolin-4-yloxy)-5,6-dimethyl-[2,3']bipyridine

HRID 228816Notes

Reaction equation

HRID 228816 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:15])[C:5]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[N:6][C:7]=1[CH3:8].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(C1C=CN=CC=1)C.ClC1C=CC=CC=1Cl>[CH3:28][O:27][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][C:23]=1[O:29][CH3:30])[N:20]=[CH:19][CH:18]=[C:17]2[O:15][C:4]1[C:5]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[N:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=1

Participants

5

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 231565165,6-Dimethyl-3-hydroxy-[2,3']bipyridine

Product 1

HCID 577564673-(6,7-Dimethoxy-quinolin-4-yloxy)-5,6-dimethyl-[2,3']bipyridineYield 84%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
140 °C

Procedure

5,6-Dimethyl-[2,3′]-bipyridin-3-ol (50 mg), 4-chloro-6,7-dimethoxyquinoline (168 mg), and 4-(N,N-dimethylamino)pyridine (92 mg) were dissolved in 1,2-dichlorobenzene (2.5 ml), and the mixture was stirred at 140° C. overnight. 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 hexane-acetone to give the title compound (81 mg, yield 84%).

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-5ac072dc42a64d18b8ef8e2ca9494d56
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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