2-Anisidine hydrochloride → 2-(6-methoxy-4-methyl-2,3-dihydro-1H-pyrrolo[3,2-c]quinolin-1-yl)phenyl methyl ether

HRID 729074

Reaktionsgleichung

Reaktionsgleichung von HRID 729074
[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][O:20][C:21]1[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=1[NH2:23]>C(O)CCC>[CH3:19][O:20][C:21]1[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=1[N:23]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 86382-Anisidine hydrochlorideHCID 33326644-Chloro-3-(2-chloroethyl)-8-methoxy-2-methylquinoline

Produkt 1

HCID 37589002-(6-methoxy-4-methyl-2,3-dihydro-1H-pyrrolo[3,2-c]quinolin-1-yl)phenyl methyl etherAusbeute 19,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

2-Methyl-3-(2-chloroethyl)-4-chloro-8-methoxyquinoline (2.70 g, 10 mmol) and 2-methoxyaniline hydrochloride (1.60 g, 10 mmol) in 1-butanol (40 ml) were heated at reflux for 6 hours then the solvent evaporated, the crude product taken up in dichloromethane, washed with aqueous sodium bicarbonate, dried and evaporated. Trituration with ether and recrystallisation from aqueous methanol gave 1-(2-methoxyphenyl)-4-methyl-6-methoxy-2,3-dihydropyrrolo[3,2-c]quinoline (0.62 g, 19%), m.p. 168°-169°.

Aufarbeitung

  1. temperatureat reflux for 6 hours
  2. customthe solvent evaporated
  3. washwashed with aqueous sodium bicarbonate
  4. customdried
  5. customevaporated
  6. customTrituration with ether and recrystallisation from aqueous methanol

Quellen und Nachweise

ORD-Eintrag
ord-a957209e9da74695bc9a53e22aa0a37d
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05051508

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