1-Chloro-2,4-Dinitrobenzene → 4-Chloro-M-phenylenediamine

HRID 423849

Reaktionsgleichung

Reaktionsgleichung von HRID 423849
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[N+:11]([O-])=O.O.O.Cl[Sn]Cl.O.C([O-])(O)=O.[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[NH2:11]

Komponenten

6

Edukt 4

HCID 61-Chloro-2,4-DinitrobenzeneHCID 962WaterHCID 61436Stannous chloride dihydrateHCID 516892Sodium Bicarbonate

Produkt 1

HCID 212094-Chloro-M-phenylenediamineAusbeute 110,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1-chloro-2,4-dinitro-benzene (100 mg, 0.5 mmol) and SnCl2.2H2O (1.12 g, 5 mmol) in ethanol (2.5 mL) was stirred at room temperature overnight. Water was added and then the mixture was basified to pH 7-8 with saturated NaHCO3 solution. The solution was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to yield 4-chloro-benzene-1,3-diamine (D-1) (79 mg, quant.). HPLC ret. time 0.38 min, 10-99% CH3CN, 5 min run; ESI-MS 143.1 m/z (MH+)

Aufarbeitung

  1. extractionThe solution was extracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-970eddd0c6a24cd2814cc3aa70bc2058
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101767B2

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