Sodium hydride → 5-(2,4-Dimethylphenyl)-3-methyl-1-(1-propylbutyl)cinnolin-4(1H)-one

HRID 598161

Reaktionsgleichung

Reaktionsgleichung von HRID 598161
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[C:11](=[O:20])[C:12]([CH3:19])=[N:13][NH:14]2.Br[CH:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25].[H-].[Na+]>CN1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[C:11](=[O:20])[C:12]([CH3:19])=[N:13][N:14]2[CH:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 704604-BromoheptaneHCID 672672585-(2,4-Dimethylphenyl)-3-methylcinnolin-4(1H)-one

Produkt 1

HCID 589385695-(2,4-Dimethylphenyl)-3-methyl-1-(1-propylbutyl)cinnolin-4(1H)-oneAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 84541-MethylpyrrolidineLösungsmittel

Versuchsvorschrift

To 0.041 g (0.16 mmol) of 5-(2,4-dimethylphenyl)-3-methylcinnolin-4(1H)-one in 0.5 mL of N-methylpyrrolidine was added 0.069 mL of 4-bromoheptane and 0.012 g (0.31 mmol) of sodium hydride (60% dispersion in mineral oil). The mixture was stirred for 75 min. at room temperature and quenched with water. The mixture was extracted with ethyl acetate and the combined organics were washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography eluting with a 8% ethyl acetate/hexanes mixture to give 0.042 g (75%) of the title compound as a light green-yellow semisolid.

Aufarbeitung

  1. customquenched with water
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe combined organics were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography
  8. washeluting with a 8% ethyl acetate/hexanes mixture

Quellen und Nachweise

ORD-Eintrag
ord-4c6d66c81a604cbdb3c98764ce69fe95
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897607B2

Verknüpfte Notizen

Wird geladen…