Nitric Acid → 5-Nitro-2-(propan-2-yl)aniline

HRID 710225Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 710225
[N+:1]([O-:4])(O)=[O:2].[CH:5]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10])([CH3:7])[CH3:6]>S(=O)(=O)(O)O>[CH:5]([C:8]1[CH:14]=[CH:13][C:12]([N+:1]([O-:4])=[O:2])=[CH:11][C:9]=1[NH2:10])([CH3:7])[CH3:6]

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 125612-Isopropylaniline

Produkt 1

HCID 189801085-Nitro-2-(propan-2-yl)anilineAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

70% HNO3 (5.1 mL, 84.76 mmol, 1.2 equiv) was added dropwise to a mixture of 2-isopropylaniline (10 mL, 9.55 g, 70.63 mmol, 1 equiv) in 70 mL of conc. sulfuric acid at 0° C. The reaction mixture was stirred at this temperature for 30 minutes and then poured onto ice. The aqueous mixture was extracted with EtOAc (2×150 mL). The organic layers were combined and washed with sat′d NaHCO3. After evaporation, the residue was purified by column chromatography on silica gel using EtOAc/hexanes (3/7) to give 2 g of product (16%) as a dark red oil.

Aufarbeitung

  1. additionpoured onto ice
  2. extractionThe aqueous mixture was extracted with EtOAc (2×150 mL)
  3. washwashed with sat′d NaHCO3
  4. customAfter evaporation
  5. customthe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-9732a4348f024ed18493c6a1f57be2a2
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181222B2

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