3-Nitro-4-(propylamino)benzonitrile → 3-Amino-4-(propylamino)benzonitrile

HRID 895511Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 895511
[CH2:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[N+:13]([O-])=O)[CH2:2][CH3:3]>C(OCC)(=O)C.[Pd]>[NH2:13][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:5]=1[NH:4][CH2:1][CH2:2][CH3:3])[C:9]#[N:10]

Komponenten

4

Edukt 1

HCID 230793333-Nitro-4-(propylamino)benzonitrile

Produkt 1

HCID 223802993-Amino-4-(propylamino)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a Parr bottle containing 4-n-propylamino-3-nitrobenzonitrile (7.63 g, 37.2 mmol) in ethyl acetate (38 mL) is added 5% Pd/C (50% wet, 633 mg). The Parr bottle is sealed in a mechanical shaker, evacuated, and then purged with nitrogen followed by hydrogen. The system is pressurized to 50 PSI of hydrogen at room temperature and mechanical shaking engaged. After 2 hours, shaking is stopped, and the system purged with nitrogen prior to opening the vessel. The reaction mixture is filtered through celite, concentrated in vacuo, and the obtained solid. recrystallized by dissolving in ethyl acetate (15 mL), heating, and adding hexanes (15 mL), to give 3-Amino-4-n-propylaminobenzonitrile as gray crystals. 1H NMR (CDCl3) δ 7.14(1H, dd), 6.92(1H, d), 6.56(1H, d), 3.98(1H, br s), 3.30(2H, br s), 3.12(2H, t), 1.75-1.65(2H, m), 1.03(3H, t). LRMS calcd 175.23, found 176.2 (MH+).

Aufarbeitung

  1. customThe Parr bottle is sealed in a mechanical shaker
  2. customevacuated
  3. custompurged with nitrogen
  4. customis pressurized to 50 PSI of hydrogen at room temperature
  5. stirringshaking
  6. customthe system purged with nitrogen
  7. filtrationThe reaction mixture is filtered through celite
  8. concentrationconcentrated in vacuo
  9. customrecrystallized
  10. dissolutionby dissolving in ethyl acetate (15 mL)
  11. temperatureheating
  12. additionadding hexanes (15 mL)

Quellen und Nachweise

ORD-Eintrag
ord-49755a26f9b54c23b45f89fb03415f57
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06916819B2

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