HCID 21654345, Verbindung → HCID 19982481, Verbindung

HRID 1460732Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1460732
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:21]=[C:20]([C:22]([OH:24])=O)[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)=[CH:8][C:7]=1[O:25][CH3:26])[CH2:2][CH2:3][CH3:4]>S(Cl)(Cl)=O>[CH2:20]([CH:19]([CH2:18][CH2:17][CH2:16][CH3:15])[CH2:14][NH:13][C:22]([C:20]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[C:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[C:7]([O:25][CH3:26])[CH:8]=2)[CH:21]=1)=[O:24])[CH3:21]

Komponenten

3

Edukt 1

HCID 21654345HCID 21654345, Verbindung

Produkt 1

HCID 19982481HCID 19982481, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

10.5 g of 2-(4'-butyoxy-3'-methoxyphenyl)quinoline-4-carboxylic acid (prepared as described in Example 7) were dissolved in 50 g of thionyl chloride, and the solution was refluxed for half an hour. The excess thionyl chloride was distilled off under reduced pressure, and the residue was introduced into 50 g of 2-ethylhexylamine with ice-water cooling. The mixture was stirred at 25° C. for 1 hour and at 80° C. for a further half hour. After cooling, 200 ml of methanol were added to dilute the mixture, and the precipitated product was washed with methanol and water and dried at 60° C. in a drying cabinet. 6.5 g were obtained of N-(2'-ethylhexyl)-2-(4'-butoxy-3'-methoxyphenyl)quinoline-4-carboxamide. The colorless crystals melt at 118° C. and have a λmax in toluene at 352 nm. In 2% strength methanolic hydrochloric acid the λmax is 403 nm.

Aufarbeitung

  1. temperaturethe solution was refluxed for half an hour
  2. distillationThe excess thionyl chloride was distilled off under reduced pressure
  3. additionthe residue was introduced into 50 g of 2-ethylhexylamine with ice-water cooling
  4. temperatureAfter cooling
  5. addition200 ml of methanol were added
  6. additionto dilute the mixture
  7. washthe precipitated product was washed with methanol and water
  8. customdried at 60° C. in a drying cabinet

Quellen und Nachweise

ORD-Eintrag
ord-e403abb66dc5495ba3df15f57065ab76
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05071987

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