Acetic Acid → N-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)isopropylideneamine

HRID 1373960Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1373960
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([NH2:22])[C:20]([CH2:23][O:24][CH2:25][CH3:26])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:29](OC)([CH3:31])[CH3:30].C(O)(=O)C>C(#N)C.C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([N:22]=[C:29]([CH3:31])[CH3:30])[C:20]([CH2:23][O:24][CH2:25][CH3:26])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 64952,2-DimethoxypropaneHCID 210757477-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-amine

Produkt 1

HCID 21075798N-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)isopropylideneamineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A suspension of 7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-amine (6.91 g, 19.8 mmol) in 55 mL of acetonitrile was treated with 2,2-dimethoxypropane (12.2 mL, 99.2 mmol) and 14 mL of glacial acetic acid. The reaction mixture was heated to 100° C. under an atmosphere of nitrogen. After 22 h, the reaction was cooled to ambient temperature and concentrated under reduced pressure to yield a brown oil. The oil was dissolved in 125 mL of CHCl3 and washed with saturated NaHCO3 solution (2×30 mL) and water (30 mL). The combined aqueous washes were back-extracted with CHCl3 (25 mL). The combined organic extracts were washed with brine (50 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield 7.69 g of N-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)isopropylideneamine as a brown solid.

Aufarbeitung

  1. temperaturethe reaction was cooled to ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. customto yield a brown oil
  4. washwashed with saturated NaHCO3 solution (2×30 mL) and water (30 mL)
  5. extractionThe combined aqueous washes were back-extracted with CHCl3 (25 mL)
  6. washThe combined organic extracts were washed with brine (50 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-968fbfba256e48c7b570aa1778666d53
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07163947B2

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