Stannous chloride dihydrate → 3-Chloro-5-methylaniline

HRID 1480725Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1480725
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([CH3:11])[CH:3]=1.O.O.Cl[Sn]Cl>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:11])[CH:3]=1

Komponenten

4

Edukt 2

HCID 61436Stannous chloride dihydrateHCID 2978873-Chloro-5-nitrotoluene

Produkt 1

HCID 124754343-Chloro-5-methylanilineAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

An ethanol solution (75 mL) containing 1-chloro-3-methyl-5-nitro-benzene (5.0 g, 29 mmol) are added with SnCl2.2H2O (32.8 g, 146 mmol). The reaction mixture was reflux for 3.0 h. The solution was concentrated under vacuum, and the residue was re-dissolved in aqueous NaOH, filtered, and extracted with EtOAc. The organic layer was collected, washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give 3-chloro-5-methyl-phenylamine (4.0 g) as light yellow solids in 97% yield: 1H NMR (500 MHz, CDCl3) δ 6.56 (s, 1H), 6.48 (s, 1H), 6.36 (s, 1H), 3.66 (bs, 2H), 2.23 (s, 3H); ESI-MS: m/z 141.7 (M+H)+.

Aufarbeitung

  1. temperatureThe reaction mixture was reflux for 3.0 h
  2. concentrationThe solution was concentrated under vacuum
  3. dissolutionthe residue was re-dissolved in aqueous NaOH
  4. filtrationfiltered
  5. extractionextracted with EtOAc
  6. customThe organic layer was collected
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-a63cd55a40c34b169ed1dee7ce72913e
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409902B2

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