Water → 2-[6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yloxy]-ethanol

HRID 228970Notes

Reaction equation

Br[CH2:2][CH2:3][OH:4].[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[OH:17])[N:13]=[CH:12][CH:11]=[C:10]2[O:18][C:19]1[C:20]([CH3:29])=[N:21][C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17][CH2:2][CH2:3][OH:4])[N:13]=[CH:12][CH:11]=[C:10]2[O:18][C:19]1[C:20]([CH3:29])=[N:21][C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 2-bromo-ethanol (226 mg) in N,N-dimethylformamide (6 ml) was added to 6-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-ol (compound 352) (100 mg) and potassium carbonate (250 mg), and the mixture was stirred at 70° C. overnight. The reaction solution was cooled to room temperature, water was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was washed with water and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-acetone to give the title compound (51.3 mg, yield 45%).

Workup

temperatureThe reaction solution was cooled to room temperature
extractionthe mixture was extracted with chloroform
washThe chloroform layer was washed with water
dry with materialwas then dried over anhydrous sodium sulfate
customThe solvent was removed by distillation under the reduced pressure
customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record: ord-32647d85e559496083c30a9e4ae943f2
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560558B2

Reaction notes

Loading…