4-Aminophenol → 4-(8-Nitroquinolin-4-yloxy)phenylamine

HRID 554480Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.CC(C)([O-])C.[K+]>CN(C)C=O.O1CCCC1>[N+:12]([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:22][C:19]1[CH:20]=[CH:21][C:16]([NH2:15])=[CH:17][CH:18]=1)([O-:14])=[O:13]

Participants

Conditions

Temperature: 110 °C

Procedure

4-Chloro-8-nitroquinoline (176 mg, 0.85 mmol) and 4-aminophenol (93 mg, 0.85 mmol) were dissolved in dimethylformamide, and to which 1.0 M potassium tert-butoxide (0.95 mL) in tetrahydrofuran was slowly added dropwise at room temperature, which was then heated and stirred at 110° C. for seven hours. When the reaction was completed, the resultant was extracted with ethyl acetate and aqueous sodium chloride, and the combined organic layers were dried with anhydrous sodium sulfate, and then filtered. The solvent was removed by vacuum distillation, and the residue was purified by a column chromatography (ethyl acetate/n-hexane=½) to obtain 140.6 mg of the desired compound as a reddish brown solid (yield 59.0%).

Workup

temperaturewhich was then heated
extractionthe resultant was extracted with ethyl acetate and aqueous sodium chloride
dry with materialthe combined organic layers were dried with anhydrous sodium sulfate
filtrationfiltered
customThe solvent was removed by vacuum distillation
customthe residue was purified by a column chromatography (ethyl acetate/n-hexane=½)

Sources & evidence

ORD record: ord-ed6a338ca328496f9397cccf1be50d07
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08049014B2

Reaction notes

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