4-Hydroxybenzaldehyde → HCID 86651748, compound

HRID 1515091Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[OH:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[F:13][C:12]([F:15])([F:14])[C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][CH:3]=[C:2]2[O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4-Chloro-8-(trifluoromethyl)quinoline (500 mg, 2.16 mmol), 4-hydroxybenzaldehyde (264 mg, 2.16 mmol), and cesium carbonate (845 mg, 2.59 mmol) were dissolved in N,N-dimethylformamide (20 mL), and the resulting mixture was stirred at 100° C. for 5 hours. Water was added to the reaction solution, and the organic matter was extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution, then dried over anhydrous magnesium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, whereby a crude product was obtained. This crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 70:30 (v/v)), whereby the objective title compound was obtained as a white solid (680 mg, yield: 99%).

Workup

extractionthe organic matter was extracted with ethyl acetate
washThe organic layer was washed with water
dry with materiala saturated sodium chloride solution, then dried over anhydrous magnesium sulfate
filtrationfiltered
distillationThen, the solvent was distilled off under reduced pressure, whereby a crude product
customwas obtained
customThis crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 70:30 (v/v)), whereby the objective title compound

Sources & evidence

ORD record: ord-43b76cbac33d4772a3a765828909bd1a
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222281B2

Reaction notes

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