2-Methylpyridin-3-ol → HCID 23078598, compound

HRID 228735Notes

Reaction equation

HRID 228735 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.[CH3:16][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>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[O:23][C:22]1[C:17]([CH3:16])=[N:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 707192-Methylpyridin-3-olHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 23078598HCID 23078598, compoundYield 100%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
135 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (245 mg), 2-methyl-3-pyridinol (227 mg), and 4-dimethylaminopyridine (420 mg) were suspended in o-dichlorobenzene (13 ml), and the suspension was stirred at 135° C. for 2 days. The reaction solution was cooled to room temperature. The solvent was then removed by distillation under the reduced pressure. The residue was purified by column chromatography using acetone-chloroform to give the title compound (324 mg, yield 100%).

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-74cbe8bbabef4601b00bece5c261dcd5
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

Loading…