Potassium Carbonate → HCID 10706966, compound

HRID 1375770Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:14])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:21][O:22][CH2:23][CH2:24]Br>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:24][CH2:23][O:22][CH3:21])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

4-Chloro-6-methoxy-7-quinolinol (50 mg), potassium carbonate (40 mg), tetra-n-butylammonium iodide (9 mg), and 2-bromoethyl methyl ether (40 mg) were dissolved in N,N-dimethylformamide (10 ml). The solution was stirred at 70° C. overnight. The solvent was removed by distillation under the reduced pressure. A saturated aqueous sodium hydrogencarbonate solution was added to the residue, followed by extraction with chloroform. The chloroform layer was dried over sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by chromatography on silica gel by development with hexane/acetone/dichloromethane (6/2/1) to give 47 mg (yield 74%) of the title compound.

Workup

customThe solvent was removed by distillation under the reduced pressure
additionA saturated aqueous sodium hydrogencarbonate solution was added to the residue
extractionfollowed by extraction with chloroform
dry with materialThe chloroform layer was dried over sodium sulfate
customThe solvent was removed by distillation under the reduced pressure
customThe residue was purified by chromatography on silica gel by development with hexane/acetone/dichloromethane (6/2/1)

Sources & evidence

ORD record: ord-13b5190d456f4effb301ef3840b57522
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07169789B2

Reaction notes

Loading…