O-Toluidine → 3-Butyryl-4-(2-methylphenylamino)-8-phthalimidoquinoline

HRID 1090671Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1090671
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][C:10]=2[N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27])(=[O:5])[CH2:2][CH2:3][CH3:4].[NH2:28][C:29]1[C:30]([CH3:35])=[CH:31][CH:32]=[CH:33][CH:34]=1>O1CCOCC1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH3:35])=[CH:13][CH:12]=[CH:11][C:10]=2[N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27])(=[O:5])[CH2:2][CH2:3][CH3:4]

Komponenten

4

Edukt 2

HCID 7242O-ToluidineHCID 100910853-Butyryl-4-chloro-8-phthalimidoquinoline

Produkt 1

HCID 104788903-Butyryl-4-(2-methylphenylamino)-8-phthalimidoquinolineAusbeute 58,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 3-butyryl-4-chloro-8-phthalimidoquinoline (61.6 g, 0.16 moles) and o-toluidine (20 ml, 0.19 mol) was heated under reflux in 1,4-dioxan (300 ml) for 3 hours. The solvent was evaporated and the residue was dissolved in chloroform, washed with dil. ammonia solution and brine. The organic solution was dried (anhyd. MgSO4) filtered and evaporated to a dark oil which crystallized on standing to give 3-butyryl-4-(2-methylphenylamino)-8-phthalimidoquinoline (42 g, 58.3%), m.p. b 170°-2° C.

Aufarbeitung

  1. temperaturewas heated
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in chloroform
  4. washwashed with dil. ammonia solution and brine
  5. dry with materialThe organic solution was dried (anhyd. MgSO4)
  6. filtrationfiltered
  7. customevaporated to a dark oil which
  8. customcrystallized

Quellen und Nachweise

ORD-Eintrag
ord-848098239eba49f383b04aef34a39fe6
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05082841

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