2-Bromo-3-pyridinol → HCID 23078502, compound

HRID 228736Notes

Reaction equation

HRID 228736 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.[Br:16][C:17]1[C:22]([OH:23])=[CH:21][CH:20]=[CH:19][N:18]=1>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[Br:16][C:17]1[C:22]([O:23][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)=[CH:21][CH:20]=[CH:19][N:18]=1

Participants

5

Reactant 2

HCID 230702-Bromo-3-pyridinolHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 23078502HCID 23078502, compoundYield 6%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
140 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (226 mg), 2-bromo-3-pyridinol (250 mg), and 4-dimethylaminopyridine (400 mg) were suspended in o-dichlorobenzene (10 ml), and the suspension was stirred at 140° C. for 2 hr. The reaction solution was cooled to room temperature, the solvent was then removed by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-chloroform to give the title compound (21 mg, yield 6%).

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 column chromatography

Sources & evidence

ORD record
ord-a78e8e9815d345d4ab26a5ba867cfd67
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

Loading…