Potassium Nitrate → 2-Tert-butyl-5-nitroaniline

HRID 73966

Reaktionsgleichung

Reaktionsgleichung von HRID 73966
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11])([CH3:4])([CH3:3])[CH3:2].[N+:12]([O-])([O-:14])=[O:13].[K+]>S(=O)(=O)(O)O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:6]=1[NH2:11])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 24434Potassium NitrateHCID 805742-tert-Butylaniline

Produkt 1

HCID 8261032-Tert-butyl-5-nitroanilineAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

To a cooled solution of sulfuric acid (90%, 50 mL) was added dropwise 2-tert-butyl-phenylamine (4.5 g, 30 mmol) at 0° C. Potassium nitrate (4.5 g, 45 mmol) was added in portions at 0° C. The reaction mixture was stirred at 0-5° C. for 5 min, poured into ice-water and then extracted with EtOAc three times. The combined organic layers were washed with brine and dried over Na2SO4. After removal of solvent, the residue was purified by recrystallization using 70% EtOH—H2O to give 2-tert-butyl-5-nitroaniline (3.7 g, 64%). 1H NMR (400 MHz, CDCl3) δ 7.56 (dd, J=8.7, 2.4 Hz, 1H), 7.48 (d, J=2.4 Hz, 1H), 7.36 (d, J=8.7 Hz, 1H), 4.17 (s, 2H), 1.46 (s, 9H); HPLC ret. time 3.27 min, 10-99% CH3CN, 5 min run; ESI-MS 195.3 m/z (MH+).

Aufarbeitung

  1. extractionextracted with EtOAc three times
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customAfter removal of solvent
  5. customthe residue was purified by recrystallization

Quellen und Nachweise

ORD-Eintrag
ord-378105a0be6248cd86bc151957c0e68f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829204B2

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