Water → HCID 24879144, compound

HRID 228698Notes

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.[OH2:16].Cl[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1Cl>CN(C)C1C=CN=CC=1>[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:16][C:18]1[CH:23]=[CH:22][C:21]([CH2:3][CH2:2][CH3:11])=[CH:20][C:19]=1[C:9](=[O:12])[CH3:8]

Participants

Conditions

Temperature: 130 °C

Procedure

2-Hydroxy-5-n-propylacetophenone (276 mg), 4-chloro-6,7-dimethoxyquinoline (117 mg), and 4-dimethylaminopyridine (191 mg) were suspended in o-dichlorobenzene (6.5 ml), and the suspension was stirred at 130° C. for 8 hr. The reaction solution was cooled to room temperature, water was then added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by thin layer chromatography using acetone-hexane to give the title compound (50 mg, yield 26%).

Workup

temperatureThe reaction solution was cooled to room temperature
extractionthe mixture was extracted with ethyl acetate
washThe ethyl acetate layer was then washed with water and saturated brine
dry with materialwas 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-a26db38e59c74e21afee2e67f53f8b84
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560558B2

Reaction notes

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