2-Toluidine hydrochloride → Ammonia

HRID 729076

Reaktionsgleichung

Reaktionsgleichung von HRID 729076
[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>[NH3:3].[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

5

Edukt 2

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

Produkt 2

HCID 222AmmoniaAusbeute 2 %HCID 196776SK&F 96079

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

2-Methyl-3-(2-chloroethyl)-4-chloro-8-methoxyquinoline (54 g, 0.2 mol), o-methylaniline hydrochloride (28.7 g, 0.2 mol) and 1-butanol (500 ml) were heated to 17° C. in a pressure vessel for 10 hours, then the solvent evaporated. Conversion to free base and chromatography (silica gel, 2% methanolic ammonia in dichloromethane) gave 1-(2-methylphenyl)-4-methyl-6-methoxy-2,3-dihydropyrrolo[3,2-c]quinoline in the early fractions. Later fractions were recrystallised from ethyl acetate to yield 1-(2-methylphenyl)-4-methyl-6-hydroxy-2,3-dihydropyrrolo[3,2-c]quinoline, m.p. 144°-146°.

Aufarbeitung

  1. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-9e7d2b29164341a0a57d405b72a80994
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05051508

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