Sodium hydride → 5,6-dihydro-6-(2-methoxycarbonylphenyl)methoxy-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline

HRID 341840Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 341840
[H-].[Na+].[C:3]1([CH2:9][CH2:10][C:11]2[N:21]3[C:22]4[C:17]([CH:18]([OH:23])[CH2:19][CH2:20]3)=[CH:16][CH:15]=[CH:14][C:13]=4[N:12]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:25][C:26]1[CH:35]=[CH:34][CH:33]=[CH:32][C:27]=1[C:28]([O:30][CH3:31])=[O:29]>CN(C)C=O>[CH3:31][O:30][C:28]([C:27]1[CH:32]=[CH:33][CH:34]=[CH:35][C:26]=1[CH2:25][O:23][CH:18]1[C:17]2[C:22]3=[C:13]([N:12]=[C:11]([CH2:10][CH2:9][C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=4)[N:21]3[CH2:20][CH2:19]1)[CH:14]=[CH:15][CH:16]=2)=[O:29]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 98604535,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-ol

Produkt 1

HCID 158384695,6-dihydro-6-(2-methoxycarbonylphenyl)methoxy-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolineAusbeute 77,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

A portion (1.15 g) of 60% sodium hydride was added to 50 mL of anhydrous N,N-dimethylformamide (DMF) in an argon atmosphere; 2.0 g of 5,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-ol obtained in Example 4 was dissolved in anhydrous DMF (40 mL) and the solution was added dropwise to the first mentioned solution at room temperature. After stirring for 1 hr at room temperature, a solution of methyl o-bromomethylbenzoate (6.6 g) in anhydrous DMF (40 mL) was added dropwise and the mixture was stirred for 1 hr. The reaction solution was poured into ice water (500 mL), and extracted with ethyl acetate, the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to yield the titled compound as a yellow oil (2.38 g).

Aufarbeitung

  1. additionthe solution was added dropwise to the
  2. customat room temperature
  3. stirringthe mixture was stirred for 1 hr
  4. extractionextracted with ethyl acetate
  5. washthe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-058f9ca9eac943eab989731895ea330a
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856334

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