2,6-Dichloro-3-nitrotoluene → 2,4-Dichloro-m-toluidine

HRID 348066

Reaktionsgleichung

Reaktionsgleichung von HRID 348066
Cl[Sn]Cl.O.[Cl:5][C:6]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[C:8]([Cl:15])[C:7]=1[CH3:16]>C(O)C>[Cl:5][C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[C:8]([Cl:15])[C:7]=1[CH3:16]

Komponenten

4

Edukt 2

HCID 971552,6-Dichloro-3-nitrotolueneHCID 43835034Tin dichloride dihydrate

Produkt 1

HCID 882822,4-Dichloro-m-toluidineAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To a solution of SnCl2.H2O (140 g, 0.62 mol) in ethanol (350 mL) was added a solution of 2,6-dichloro-3-nitrotoluene (25 g, 0.12 mol) in ethanol (50 mL). The reaction mixture was refluxed for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in water (100 mL), pH was adjusted to approximately pH 12 with 1N NaOH solution and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over sodium sulfate, and concentrated to afford 2,6-dichloro-3-aminotoluene (21 g, 98%); NMR (CDCl3) 2.42 (s, 3), 6.62 (d, 1), 7.14 (d, 1) ppm.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in water (100 mL)
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-059ce2e0c0144c7f816cb39769fdae6a
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176207B2

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