Methoxyacetic Acid → 2-Methoxymethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

HRID 1599737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1599737
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:17][O:18][CH2:19][C:20](O)=O.[OH-].[Na+]>O>[CH3:17][O:18][CH2:19][C:20]1[N:12]([CH2:13][CH:14]([CH3:16])[CH3:15])[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]=1

Komponenten

5

Edukt 3

HCID 12251Methoxyacetic AcidHCID 14798Sodium HydroxideHCID 11298872N4-(2-methylpropyl)quinoline-3,4-diamine

Produkt 1

HCID 152244182-Methoxymethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

3-Amino-4-(2-methylpropylamino)quinoline (5.0 g; 0.023 mol) and methoxyacetic acid (20 mL) were mixed and heated at about 200° C. until all bubbling had stopped. Heating was continued for 5-10 min longer and the dark solution was allowed to cool to room temperature. The solution was diluted with water, made strongly basic with 50% sodium hydroxide and extracted with ether. The combined extracts were dried over magnesium sulfate and evaporated to dryness to yield 5.2 g of crude product. The crude product was used as such for further reactions. A small sample was recrystallized from ether to yield nearly colorless crystals, m.p. 96°-99° C. Analysis: Calculated: C, 71.4; H, 7.1; N, 15.6. Found: C, 71.1; H, 7.0; N, 15.6.

Aufarbeitung

  1. temperatureHeating
  2. temperatureto cool to room temperature
  3. extractionextracted with ether
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-bc98b2a14b4043e8a7b280e174ff874c
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05741909

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