Toluene → HCID 178461186, Verbindung

HRID 1624051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1624051
[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:4][C:3]1=O.[C:17]1(C)C=CC=CC=1.[NH2:24][NH2:25]>CO>[CH3:1][C@@H:2]1[C:7]2[C:6](=[CH:17][NH:24][N:25]=2)[C@@H:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 9321HydrazineHCID 71114860HCID 71114860, Verbindung

Produkt 1

HCID 178461186HCID 178461186, VerbindungAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

(+/−)-(trans)-4-(4-Methyl-3-oxo-cyclohexyl)benzonitrile (0.55 g, 2.58 mmol) is added to toluene (10.0 mL) and tert-butoxybis(dimtheylamino)methane (0.67 mL, 3.22 mmols) and stirred at 120° C. for 16 hours. The mixture is cooled to room temperature and concentrated in vacuo. The residue is added to MeOH (10.0 mL) and hydrazine (0.07 mL, 2.32 mmol) and stirred at 80° C. for 1.0 hour. The mixture is cooled to room temperature and concentrated in vacuo. The residue is purified by silica gel chromatography (35%-55% EtOAc/hexanes) to give (+/−)-(trans)-4-[7-methyl-4,5,6,7-tetrahydro-2H-indazol-4-yl]benzonitrile (0.18 g, 29%).

Aufarbeitung

  1. temperatureThe mixture is cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. stirringstirred at 80° C. for 1.0 hour
  4. temperatureThe mixture is cooled to room temperature
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by silica gel chromatography (35%-55% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-bfe1de860ec440c3800ae5b5e8d43fee
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778984B2

Notizen zur Reaktion

Wird geladen…