Ammonium Chloride → 1,3-Benzenediamine, 2-methoxy-

HRID 131078

Reaktionsgleichung

Reaktionsgleichung von HRID 131078
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:5]=1[O:13][CH3:14])([O-])=O.[NH4+].[Cl-]>O.[Zn]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[O:13][CH3:14]

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 5977192,6-Dinitrophenyl methyl ether

Produkt 1

HCID 124029761,3-Benzenediamine, 2-methoxy-Ausbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

0.500 g (2.52 mmol) of compound 2,6-dinitroanisole was suspended in 40 mL of water together with 2.310 g (35.3 mmol) of Zn and 0.530 g (10.1 mmol) of NH4Cl. The solution was boiled for 2.5 h. After cooling to room temperature, the solution was extracted with ethyl acetate. The organic solution was dried with anhydrous Na2SO4 and distilled in vacuo to obtain 0.330 g (95%) of clean 2,6-diaminoanisole as a red oil. 1H NMR (CDCl3) δ 6.73 (t, J=7.9 Hz, 1H, Ar—H), 6.19 (d, J=7.9 Hz, 2H, Ar—H), 3.78 (s, 3H, O—CH3), 3.73 (br. s, 4H, Ar—NH2). 13C NMR (CDCl3) δ 140.3, 134.9, 125.2, 106.6, 58.6.

Aufarbeitung

  1. extractionthe solution was extracted with ethyl acetate
  2. dry with materialThe organic solution was dried with anhydrous Na2SO4
  3. distillationdistilled in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6f19936467724c4395edc034ea960fd7
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384789B2

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