Water → 5-Amino-2-isobutoxybenzonitrile

HRID 1744515

Reaktionsgleichung

Reaktionsgleichung von HRID 1744515
[Cl-].[NH4+].[OH2:3].C([C:8]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:9]=1[C:10]#[N:11])C(C)C>[Fe].C(O)C>[NH2:16][C:13]1[CH:14]=[CH:15][C:8]([O:3][CH2:8][CH:9]([CH3:12])[CH3:10])=[C:9]([CH:12]=1)[C:10]#[N:11]

Komponenten

6

Edukt 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 222280302-Isobutyl-5-nitrobenzonitrile

Produkt 1

HCID 193660285-Amino-2-isobutoxybenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Ammonium chloride (5.6 g) and iron powder (21 g) were added to a mixed solvent of water (80 ml) and ethanol (240 ml), and the mixture was heated to 65° C. Then, 2-isobutyl-5-nitrobenzonitrile (20 g) was added in parts over 20 min and the mixture was stirred at a refluxing temperature for 30 min. The reaction mixture was ice-cooled and filtrated. The solvent was evaporated under reduced pressure. To the residue was added aqueous sodium hydroxide solution and the mixture was extracted with toluene. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, after which the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to allow crystallization. The crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane to give the title compound (17 g), melting point: 88–93° C.

Aufarbeitung

  1. temperaturecooled
  2. filtrationfiltrated
  3. customThe solvent was evaporated under reduced pressure
  4. additionTo the residue was added aqueous sodium hydroxide solution
  5. extractionthe mixture was extracted with toluene
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customafter which the solvent was evaporated under reduced pressure
  9. additionDiisopropyl ether was added to the residue
  10. customcrystallization
  11. customThe crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-aee6f7b30eba439eaa55ab5f9e4e988c
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07015218B1

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