4-Chloro-6,7-dimethoxyquinoline → HCID 22132715, compound

HRID 1857124Notes

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.[CH:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1[C:26]([C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)=[O:27]>>[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:34][C:31]1[CH:32]=[CH:33][C:28]([C:26]([C:17]2[CH:18]=[CH:19][C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=2)=[O:27])=[CH:29][CH:30]=1

Participants

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinoline

HCID 15640646HCID 15640646, compound

Product 1

HCID 22132715HCID 22132715, compoundYield 23%

Conditions

Temperature: 180 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (112 mg) and 4-hydroxyphenyl 2-naphthyl ketone (124 mg) obtained in Example 36 were mixed and stirred at 180° C. for 30 minutes. The reaction mixture was partitioned between saturated aqueous sodium hydrogen carbonate and chloroform, and then the chloroform layer was dried with anhydrous magnesium sulfate. After removing the solvent by reduced-pressure distillation, a portion (50 mg) of the resulting residue (227 mg) was purified by thin layer chromatography on silica gel eluting with chloroform/ethyl acetate (5/1) to obtain 11 mg of the title compound (yield: 23%).

Workup

customThe reaction mixture was partitioned between saturated aqueous sodium hydrogen carbonate and chloroform
dry with materialthe chloroform layer was dried with anhydrous magnesium sulfate
customAfter removing the solvent
distillationby reduced-pressure distillation
customa portion (50 mg) of the resulting residue (227 mg) was purified by thin layer chromatography on silica gel eluting with chloroform/ethyl acetate (5/1)

Sources & evidence

ORD record: ord-11442cdf0a4e4bae8d3eeab06a566ca6
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06143764

Reaction notes

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