5-Chloro-2-nitroanisole → Benzenamine, 4-chloro-2-methoxy-

HRID 272757Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 272757
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[C:4]([O:11][CH3:12])[CH:3]=1>CO.[Pt]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([O:11][CH3:12])[CH:3]=1

Komponenten

4

Edukt 1

HCID 811105-Chloro-2-nitroanisole

Produkt 1

HCID 7143Benzenamine, 4-chloro-2-methoxy-Ausbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

4-Chloro-2-methoxynitrobenzene (2.8 g, 14.9 mmol) was dissolved in MeOH (110 mL), then 5% platinum on carbon (0.61 g) was added and the reaction stirred under a H2 balloon for 4 hours. The reaction was then filtered through diatomaceous earth (Celite®) and concentrated under vacuum, giving the product (2.3 g, 100%) as syrup that slowly solidified. MS (DCI) m/e 158 & 160 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 6.83 (d, J=2.4 Hz, 1H), 6.71 (dd, J=8.5, 2.4 Hz, 1H), 6.63 (d, J=8.5 Hz, 1H), 5.27 (v br s, 2H), 3.77 (s, 3H).

Aufarbeitung

  1. filtrationThe reaction was then filtered through diatomaceous earth (Celite®)
  2. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5606f23031d0411485b876b09ff28398
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456169B2

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