6-Hydroxymethyl-4-isobutyl-1,4-dihydro-quinoline-3-carbonitrile → 6-Formyl-4-isobutyl-quinoline-3-carbonitrile

HRID 1297672Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1297672
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]([C:13]#[N:14])[CH:6]2[CH2:15][CH:16]([CH3:18])[CH3:17]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([C:13]#[N:14])=[C:6]2[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:1]

Komponenten

4

Edukt 1

HCID 585857716-Hydroxymethyl-4-isobutyl-1,4-dihydro-quinoline-3-carbonitrile

Produkt 1

HCID 585858466-Formyl-4-isobutyl-quinoline-3-carbonitrileAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To the solution of 6-hydroxymethyl-4-isobutyl-1,4-dihydro-quinoline-3-carbonitrile (200 mg, 0.83 mmol) in chloroform (6 mL) was added manganese dioxide (300 mg). The mixture was stirred at reflux for 10 h. After removal of the solid by filtration, the filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 0%-30% ethyl acetate in hexanes in 30 min) afforded 6-formyl-4-isobutyl-quinoline-3-carbonitrile (110 mg, 56%) as a white solid. LC-MS m/e 239 (MH+).

Aufarbeitung

  1. temperatureat reflux for 10 h
  2. customAfter removal of the solid
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1154d6301b674925ae73ea6e38ed6be2
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07250515B2

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