Water → HCID 10599688, compound

HRID 369428Notes

Reaction equation

[OH:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]2[O:7][C:8]3[C:13]([C:14](=[O:16])[CH:15]=2)=[CH:12][CH:11]=[CH:10][C:9]=3[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:4][CH:3]=1.Cl[CH2:25][C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:20]([O:19][C:17]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[O:7][C:6]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:25][C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]=3)=[CH:23][CH:22]=1)=[CH:15][C:14]2=[O:16])=[O:18])[CH3:21]

Participants

Conditions

Temperature: 100 °C

Procedure

4'-Hydroxy-8-ethoxycarbonylflavone (1 eq.) and 2-chloromethylquinoline (1.1 eq.) were dissolved in DMF, followed by the addition of potassium carbonate (1.2 eq.). The resulting mixture was stirred at 100° C. and, subsequent to the completion of the reaction, was charged into water. The water layer was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was recrystallized from DMF-ethanol, whereby the title compound represented by the following formula was obtained (yield: 64%). ##STR21##

Workup

extractionThe water layer was extracted with ethyl acetate
washThe organic layer was washed with water
dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was recrystallized from DMF-ethanol, whereby the title compound
customwas obtained (yield: 64%)

Sources & evidence

ORD record: ord-a48fac0665c6484fbce841519a8805dc
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06136848

Reaction notes

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