HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

1,2-Dichlorobenzene → 4-(5-Chloro-7-methyl-quinolin-6-yloxy)-6,7-dimethoxy-quinoline

HRID 228881
Notes
Print preview

Reaction equation

HRID 228881 reaction equation
Br[C:2]1[C:11]([OH:12])=[C:10]([CH3:13])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.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.[Cl:29]C1C=CC=CC=1Cl>CN(C)C1C=CN=CC=1>[Cl:29][C:2]1[C:11]([O:12][C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[C:10]([CH3:13])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 72391,2-DichlorobenzeneHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 230783095-Bromo-6-hydroxy-7-methyl-quinoline

Product 1

HCID 230783154-(5-Chloro-7-methyl-quinolin-6-yloxy)-6,7-dimethoxy-quinolineYield 10%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
140 °C

Procedure

5-Bromo-6-hydroxy-7-methyl-quinoline (110 mg), 4-chloro-6,7-dimethoxyquinoline (330 mg), and 4-dimethylaminopyridine (240 mg) were suspended in o-dichlorobenzene (10 ml), and the mixture was stirred at 140° C. for 6 hr. 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 thin layer chromatography using acetone-chloroform to give the title compound (19 mg, yield 10%).

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 thin layer chromatography

Sources & evidence

ORD record
ord-c6d4e4992f244669b0443c109f795087
Source dataset
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07560558B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes