Potassium Nitrate → 4-(Tert-butyl)-3-nitroaniline

HRID 401359Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 401359
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N+:12]([O-])([O-:14])=[O:13].[K+].C([O-])(O)=O.[Na+]>OS(O)(=O)=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([NH2:11])=[CH:9][C:10]=1[N+:12]([O-:14])=[O:13])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 24434Potassium NitrateHCID 698614-Tert-ButylanilineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 3161634-(Tert-butyl)-3-nitroanilineAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

To a mixture of 4-tert-butyl-phenylamine (10.0 g, 67.01 mmol) dissolved in H2SO4 (98%, 60 mL) was slowly added KNO3 (8.1 g, 80.41 mmol) at 0° C. After addition, the reaction was allowed to warm to room temperature and stirred overnight. The mixture was then poured into ice-water and basified with sat. NaHCO3 solution to pH 8. The mixture was extracted several times with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography (petroleum ether-EtOAc, 10:1) to give 4-tert-butyl-3-nitro-phenylamine (10 g, 77%).

Aufarbeitung

  1. customat 0° C
  2. additionAfter addition
  3. extractionThe mixture was extracted several times with CH2Cl2
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (petroleum ether-EtOAc, 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-16bcd6bdeaf744fcbc62e8763d316df9
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741925B2

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