Hydrazine → (2R)-2-(4-nitrophenyl)propan-1-amine

HRID 392929Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 392929
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([CH3:23])[CH2:11][N:12]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].NN>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C@@H:10]([CH3:23])[CH2:11][NH2:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 9321HydrazineHCID 113927422-[(2R)-2-(4-nitrophenyl)propyl]isoindoline-1,3-dione

Produkt 1

HCID 51434705(2R)-2-(4-nitrophenyl)propan-1-amineAusbeute 97,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A 250 mL three necked round bottom flask equipped with a mechanical stirrer, thermometer, reflux condenser and addition funnel is charged with 2-[(2R)-2-(4-nitrophenyl)propyl]isoindoline-1,3-dione (25.02 g, 80.6 mmol) and toluene (200.0 mL). To this solution at room temperature was added anhydrous hydrazine (7.08 mL, 226.0 mmol). Reaction exothermed slightly and was stirred for 45 minutes, heated at 90° C.-95° C. until the disappearance of starting material. A massive precipitate formed by the end of the reaction. Cooled to room temperature and chilled to 0° C. before filtration. Concentration of the filtrate afforded (2R)-2-(4-nitrophenyl)propylamine (14.11 g, 97%) as an oil;

Aufarbeitung

  1. temperaturethermometer, reflux
  2. additioncondenser and addition funnel
  3. customReaction
  4. temperatureheated at 90° C.-95° C. until the disappearance of starting material
  5. customA massive precipitate formed by the end of the reaction
  6. temperaturechilled to 0° C. before filtration

Quellen und Nachweise

ORD-Eintrag
ord-f96b2e03314a4b1a930db96140aefba0
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06803484B2

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