2-Toluidine hydrochloride → SK&F 96079

HRID 729075

Reaktionsgleichung

Reaktionsgleichung von HRID 729075
[CH3:1][C:2]1[C:11]([CH2:12][CH2:13]Cl)=[C:10](Cl)[C:9]2[C:4](=[C:5]([O:16][CH3:17])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.Cl.[CH3:19][C:20]1[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=1[NH2:22]>C(O)CCC>[CH3:19][C:20]1[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=1[N:22]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([O:16][CH3:17])[C:4]=3[N:3]=[C:2]([CH3:1])[C:11]=2[CH2:12][CH2:13]1

Komponenten

4

Edukt 2

HCID 124842-Toluidine hydrochlorideHCID 33326644-Chloro-3-(2-chloroethyl)-8-methoxy-2-methylquinoline

Produkt 1

HCID 196776SK&F 96079Ausbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

2-Methyl-3-(2-chloroethyl)-4-chloro-8-methoxyquinoline (8.37 g, 31 mmol) and 2-methylaniline hydrochloride (4.45 g, 31 mmol) in 1-butanol (100 ml) were heated at reflux for 5 days, then the solvent evaporated, the crude product taken up in dichloromethane, washed with aqueous sodium bicarbonate, dried and evaporated. Chromatography (silica gel, 2% methanolic ammonia in dichloromethane) and recrystallisation from aqueous ethanol gave 1-(2-methylphenyl)-4-methyl-6-methoxy-2,3-dihydropyrrolo[3,2-c]quinoline (2.04 g, 22 %), m.p. 182°-183°.

Aufarbeitung

  1. temperatureat reflux for 5 days
  2. customthe solvent evaporated
  3. washwashed with aqueous sodium bicarbonate
  4. customdried
  5. customevaporated
  6. customChromatography (silica gel, 2% methanolic ammonia in dichloromethane) and recrystallisation from aqueous ethanol

Quellen und Nachweise

ORD-Eintrag
ord-2edeca0174b046659926189dfbd51726
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05051508

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