Ethanol → 3-(1-Amino-2-naphthoyl)benzonitrile

HRID 1191304Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1191304
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[C:14]([C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[C:19]#[N:20])=[O:15])([O-])=O.C(O)C.O>C(O)(=O)C.[Fe]>[NH2:1][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[C:14]([C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[C:19]#[N:20])=[O:15]

Komponenten

6

Edukt 3

HCID 702EthanolHCID 962WaterHCID 866904463-(1-Nitro-2-naphthoyl)benzonitrile

Produkt 1

HCID 866904473-(1-Amino-2-naphthoyl)benzonitrileAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

3-(1-nitro-2-naphthoyl)benzonitrile (6.22 g, 20.6 mmol) was dissolved at 65° C. in acetic acid (150 mL), ethanol (150 mL) and water (15 mL). After cooled to room temperature, to the solution was added iron powder (6.67 g, 119 mmol). To the mixture was stirred at 65° C. for 1 hour, and cooled to room temperature. The resultant mixture was added silica gel (100 g), filtered, and the residue was washed with ethyl acetate. The filtrate and washings were combined, washed with a saturated aqueous sodium bicarbonate solution and saturated brine. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform), to give the titled compound as a yellow crystal (5.40 g, yield 96%).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. washthe residue was washed with ethyl acetate
  4. washwashed with a saturated aqueous sodium bicarbonate solution and saturated brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-f195748a06654646acb3b4883869c4b5
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680110B2

Notizen zur Reaktion

Wird geladen…