Sodium Hydroxide → 4-Cyclopentylbenzene-1,2-diamine

HRID 1424223Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1424223
[CH:1]1([C:6]2[CH:11]=[CH:10][C:9]([NH:12]C(=O)C)=[C:8]([N+:16]([O-])=O)[CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>[Pd]>[CH:1]1([C:6]2[CH:7]=[C:8]([NH2:16])[C:9]([NH2:12])=[CH:10][CH:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 86699135N-(4-cyclopentyl-2-nitrophenyl)acetamide

Produkt 1

HCID 866990854-Cyclopentylbenzene-1,2-diamineAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A suspension of N-(4-cyclopentyl-2-nitrophenyl)acetamide (Preparation 86, 19.48 g, 78.46 mmol) in aqueous sodium hydroxide (6.0M, 100 mL, 600 mmol) was heated at 90° C. for 4 days. The reaction was allowed to cool and extracted with methylene chloride (3×). The organic layers were combined, dried over anhydrous magnesium sulphate, filtered, and concentrated in vacuo. The resulting residue was suspended in methanol (300 mL) and treated with palladium (2 g, 20 mmol, 10% on carbon, Degussa type). The reaction mixture was hydrogenated at 40 psi for 5 hours before filtering through celite and concentrating in vacuo. The residue was purified using silica gel column chromatography eluting with a 0-100% ethyl acetate/hexanes gradient to afford the title compound (6.85 g, 50%) as a purple solid.

Aufarbeitung

  1. temperatureto cool
  2. extractionextracted with methylene chloride (3×)
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. filtrationbefore filtering through celite
  7. concentrationconcentrating in vacuo
  8. customThe residue was purified
  9. washeluting with a 0-100% ethyl acetate/hexanes gradient

Quellen und Nachweise

ORD-Eintrag
ord-982a0095b5f6425aa2be6f3be4760afe
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927587B2

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