Methoxyacetic Acid → alpha,alpha-Dimethyl-2-methoxymethyl-1H-imidazo[4,5-c]quinoline-1-ethanol

HRID 274396

Reaktionsgleichung

[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([OH:17])([CH3:16])[CH3:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:18][O:19][CH2:20][C:21](O)=O>C(OCC)(=O)C>[CH3:16][C:14]([CH3:15])([OH:17])[CH2:13][N:12]1[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=[C:21]1[CH2:20][O:19][CH3:18]

Komponenten

Reaktionsbedingungen

Temperatur: 170 °C

Versuchsvorschrift

3-Amino-4-(2-hydroxy-2-methylpropylamino)quinoline (7.5 g, 32 mmol) was combined with methoxyacetic acid (7.5 mL, 97 mmol) and heated at about 170° C. for about 3 hours. The resulting solid residue was dissolved in ethyl acetate (150 mL). The ethyl acetate solution was extracted twice with 0.2N sodium hydroxide, washed with water, dried over magnesium sulfate, treated with activated charcoal and then concentrated to a volume of about 50 mL. Hexane was added to the ethyl acetate and the resulting precipitate was collected and dried to provide 0.9 g of the desired product as a crystalline solid, m.p. 145°-148° C.

Aufarbeitung

extractionThe ethyl acetate solution was extracted twice with 0.2N sodium hydroxide
washwashed with water
dry with materialdried over magnesium sulfate
additiontreated with activated charcoal
concentrationconcentrated to a volume of about 50 mL
additionHexane was added to the ethyl acetate
customthe resulting precipitate was collected
customdried

Quellen und Nachweise

ORD-Eintrag: ord-3d10098f09b04188a27c419d4b6f03fd
Quelldatensatz: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05389640

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