2-Toluidine hydrochloride → 4,6-Dimethyl-1-o-tolyl-2,3-dihydro-1H-pyrrolo[3,2-c]quinoline

HRID 729078

Reaktionsgleichung

Reaktionsgleichung von HRID 729078
[CH3:1][C:2]1[C:11]([CH2:12][CH2:13]Cl)=[C:10](Cl)[C:9]2[C:4](=[C:5]([CH3:16])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.Cl.[CH3:18][C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[NH2:21]>C(O)CCC>[CH3:18][C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[N:21]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([CH3:16])[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 8203234-Chloro-3-(2-chloroethyl)-2,8-dimethylquinoline

Produkt 1

HCID 167272544,6-Dimethyl-1-o-tolyl-2,3-dihydro-1H-pyrrolo[3,2-c]quinolineAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

2,8-Dimethyl-3-(2-chloroethyl)-4-chloroquinoline (7.63 g, 30 mmol) and 2-methylaniline hydrochloride (4.31 g, 30 mmol) in 1-butanol (100 ml) wereheated at reflux for 4 days, then the solvent evaporated, the crude producttaken 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)-4,6-dimethyl-2,3-dihydropyrrolo-[3,2-c]quinoline (1.95 g, 23%), m.p. 126°-128°.

Aufarbeitung

  1. temperatureat reflux for 4 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-2d724d9f195a4d3a93f40835be6a25c8
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05051508

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