Water → N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,6-dimethylphenyl]quinoline-6-carboxamide

HRID 70805

Reaktionsgleichung

Reaktionsgleichung von HRID 70805
[F:1][C:2]([F:19])([F:18])[C:3]([C:9]1[CH:15]=[C:14]([CH3:16])[C:12]([NH2:13])=[C:11]([CH3:17])[CH:10]=1)([F:8])[C:4]([F:7])([F:6])[F:5].[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH2:26]>ClCCl>[F:1][C:2]([F:18])([F:19])[C:3]([C:9]1[CH:15]=[C:14]([CH3:16])[C:12]([NH:13][C:4]([C:3]2[CH:2]=[C:24]3[C:25](=[CH:10][CH:9]=2)[N:20]=[CH:21][CH:22]=[CH:23]3)=[O:26])=[C:11]([CH3:17])[CH:10]=1)([F:8])[C:4]([F:7])([F:6])[F:5]

Komponenten

5

Edukt 3

HCID 962WaterHCID 1049PyridineHCID 98824254-(1,1,1,2,3,3,3-Heptafluoropropan-2-yl)-2,6-dimethylaniline

Produkt 1

HCID 86672963N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,6-dimethylphenyl]quinoline-6-carboxamideAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Quinoline-6-carboxylic acid (1.0 g) was dissolved in dichloromethane. N,N-dimethylformamide (300 μL) and oxalyl chloride (1.2 g) were added to this solution at room temperature and stirred for two hours followed by reflux for 20 minutes. The solvent was removed under the reduced pressure, and quinoline-6-carbonyl chloride was obtained as a crude product, which was then dissolved in dichloromethane. To this solution, 4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,6-dimethylaniline (1.6 g) dissolved in dichloromethane and pyridine (1.2 g) were added and stirred at room temperature for 5 hours. The reaction solution was diluted with water and extracted twice with ethyl acetate. The organic phases were combined and washed with 1N hydrochloric acid and water, and dried over anhydrous magnesium sulfate. The drying agent (anhydrous magnesium sulfate) was removed by filtration and the solvent was distilled off under the reduced pressure. The residue was purified by column chromatography to obtain N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,6-dimethylphenyl]quinoline-6-carboxamide (2.0 g, yield 78%).

Aufarbeitung

  1. extractionextracted twice with ethyl acetate
  2. washwashed with 1N hydrochloric acid and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe drying agent (anhydrous magnesium sulfate) was removed by filtration
  5. distillationthe solvent was distilled off under the reduced pressure
  6. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d855bb5b0d594f0cac7ac30fbe15706e
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822691B2

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