Benzyl Bromide → 1-Benzyl-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

HRID 277337Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 277337
[NH:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH2:4][N:3]3[C:2]1=[O:13].CC(C)([O-])C.[K+].C1COCC1.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C.O.C(OC)(C)(C)C>[CH2:25]([N:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH2:4][N:3]3[C:2]1=[O:13])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

8

Edukt 4

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 127895324H-Imidazo[4,5,1-ij]quinolin-2(1H)-oneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 97952141-Benzyl-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

A mixture of 4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (I, J. Heterocyclic Chem., 19, 837-49 (1982), 1.0g, 5.8mmol) in DMF (10 ml) is cooled to 0° and treated with potassium t-butoxide in THF (1.98 M, 3.2 ml, 6.3 mmol) maintaining the reaction temperature at 0°. The resulting mixture is stirred at 0° for 10 minutes. Benzyl bromide (0.73 ml, 6.1 mmol) is then added while maintaining the reaction temperature at methyl t-butyl ether (MTBE) from water followed by several water washes. The MTBE phase is concentrated under reduced pressure. The concentrate is cooled to 0°, filtered and washed two times with 0° MTBE. The product is dried at 50° under reduced pressure with a nitrogen purge to give the title compound, CMR (CDCl3, 100 MHz) 153.78, 136.44, 128.69, 127.67, 127.60, 126.73, 125.86, 122.90, 122.78, 121.28, 116.92, 116.17, 108.36,44.95 and 42.37 δ.

Aufarbeitung

  1. temperatureis cooled to 0°
  2. temperaturemaintaining the reaction temperature at 0°
  3. concentrationThe MTBE phase is concentrated under reduced pressure
  4. temperatureThe concentrate is cooled to 0°
  5. filtrationfiltered
  6. washwashed two times with 0° MTBE
  7. customThe product is dried at 50° under reduced pressure with a nitrogen
  8. custompurge

Quellen und Nachweise

ORD-Eintrag
ord-67b0b648ec064cababc28b8f2b6639e2
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355802B1

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