Triethylamine → N-[4-(8-nitroquinolin-4-yloxy]phenyl]-4-chloro-3-trifluoromethylbenzamide

HRID 554483Notes

Reaction equation

HRID 554483 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[C:9]2[O:14][C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1)([O-:3])=[O:2].ON1C2C=CC=CC=2N=N1.[Cl:32][C:33]1[CH:41]=[CH:40][C:36]([C:37](O)=[O:38])=[CH:35][C:34]=1[C:42]([F:45])([F:44])[F:43].C(N(CC)CC)C>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[C:9]2[O:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:37](=[O:38])[C:36]2[CH:40]=[CH:41][C:33]([Cl:32])=[C:34]([C:42]([F:45])([F:43])[F:44])[CH:35]=2)=[CH:17][CH:16]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27738574-Chloro-3-(trifluoromethyl)benzoic acidHCID 533302934-(8-Nitroquinolin-4-yloxy)phenylamine

Product 1

HCID 59509413N-[4-(8-nitroquinolin-4-yloxy]phenyl]-4-chloro-3-trifluoromethylbenzamideYield 71.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-(8-Nitroquinolin-4-yloxy)phenylamine (103 mL, 0.46 mmol), N-hydroxybenzotriazole (HOBt) (62 mg, 0.46 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarboimide (EDCl) (102 mg, 0.53 mmol) and 4-chloro-3-trifluoromethylbenzoic acid (103 mg, 0.46 mmol) were dissolved in dimethylformamide (3.6 mL), and to which triethylamine was added dropwise at room temperature, which was then heated and stirred at 80° C. When the reaction was completed, the resultant was extracted with ethyl acetate and saturated sodium bicarbonate, 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 125 mg of the desired compound as a brown solid (yield 71.2%).

Workup

  1. temperaturewhich was then heated
  2. extractionthe resultant was extracted with ethyl acetate and saturated sodium bicarbonate
  3. dry with materialwere dried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed by vacuum distillation
  6. customthe residue was purified by a column chromatography (ethyl acetate/n-hexane=½)

Sources & evidence

ORD record
ord-b6414f0a90784209abb7b89a2647801e
Source dataset
uspto-grants-2011_11
Patent number
US08049014B2

Reaction notes

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