Water → 6-Hydroxy-4-phenyl-2-propylquinoline-3-carbonitrile

HRID 1986429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1986429
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][Si](C(C)(C)C)(C)C)=[CH:4][C:3]=1[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O.O=[C:25]([CH2:29][CH2:30][CH3:31])[CH2:26][C:27]#[N:28].CS(O)(=O)=O.O>C1(C)C=CC=CC=1>[OH:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[N:1]=[C:25]([CH2:29][CH2:30][CH3:31])[C:26]([C:27]#[N:28])=[C:16]2[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 97937233-OxohexanenitrileHCID 68832602(2-Amino-5-{[tert-butyl(dimethyl)silyl]oxy}-phenyl)(phenyl)methanone

Produkt 1

HCID 688333146-Hydroxy-4-phenyl-2-propylquinoline-3-carbonitrileAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of (2-amino-5-{[tert-butyl(dimethyl)silyl]oxy}-phenyl)(phenyl)methanone (2.0 g, 6.1 mmol), 3-oxohexanenitrile (0.81 g, 7.3 mmol) and methanesulfonic acid (0.59 g, 6.1 mmol) in toluene (50 ml) was stirred at 110° C. for 15 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was crystallized from disopropyl ether to give 6-hydroxy-4-phenyl-2-propylquinoline-3-carbonitrile (0.98 g, yield 56%) as pale-yellow crystals.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was crystallized from disopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-ff61c76a1bb24130b897e26ad54355ac
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07547710B2

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