Water → N-Methyl-o-phenylenediamine

HRID 54320

Reaktionsgleichung

Reaktionsgleichung von HRID 54320
[Cl-].[Cl-].[Ca+2].O.FC1C=CC(N)=C(N)C=1.[CH3:14][NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-])=O>CCO.CCOCC.[Zn]>[CH3:14][NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH2:22]

Komponenten

8

Edukt 4

HCID 962WaterHCID 69157Benzenamine, N-methyl-2-nitro-HCID 1645844-Fluorobenzene-1,2-diamine2×HCID 5284359Calcium Chloride

Produkt 1

HCID 78498N-Methyl-o-phenylenediamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 702EthanolLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

N-Methyl-1,2-diaminobenzene was prepared using an adaptation of the method of Tsuji et al. (J. Org. Chem. 55:580 (1990)). Zn powder (8.07 g, 0.123 mol), CaCl2 (807 mg), H2O (9.9 mL) and 30 mL EtOH were combined and brought to reflux as described for 4-fluoro-1,2-diaminobenzene (see Example 10), and to this mixture was added slowly dropwise a solution of N-methyl-2-nitroaniline (1.50 g, 9.86 mmol) in 15 mL EtOH. Analysis and workup were as described for 4-fluoro-1,2-diaminobenzene except that the reaction residue was dissolved in 50 ml Et2O. This Et2O solution was then extracted with 3×25 mL 1N HCl and the aqueous layers combined and basified with 5 g of 50% NaOH solution. This solution was then extracted with 3×25 mL Et2O. These Et2O layers were then combined, dried (MgSO4) and the solvent evaporated at reduced pressure to yield 911.1 mg (76.1%) of a dark brown oil. 1H NMR (CDCl2) δ2.87 (s, 3H, CH3), 3.31 (br s, 3H, NH), 6.67 (m, 3H, ArH), 6.86 (m, 1H, ArH).

Aufarbeitung

  1. temperatureto reflux
  2. extractionThis Et2O solution was then extracted with 3×25 mL 1N HCl
  3. extractionThis solution was then extracted with 3×25 mL Et2O
  4. dry with materialdried (MgSO4)
  5. customthe solvent evaporated at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-929d94df6f224bab9b8489fe3fdd290f
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622952

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