Reaktion #77249

ord-3a167c5fbae7426ea028dfb8a0430b08

Reaktionsgleichung

[NH4+].[OH-]
ammonium hydroxide
O=C(c1cccnc1)c1ccccc1Cl
o-chlorophenyl 3-pyridyl ketone
O=S(=O)(O)O
sulfuric acid
O=[N+]([O-])O
nitric acid
O=S(=O)(O)O
sulfuric acid
→
O=C(c1cccnc1)c1cc([N+](=O)[O-])ccc1Cl
title compound
Ausbeute 94.2%
O=C(c1cccnc1)c1cc([N+](=O)[O-])ccc1Cl
3-(2-Chloro-5-nitrobenzoyl)pyridine
Ausbeute 94.2%

Edukte

—
resultant mixture
[NH4+].[OH-]
ammonium hydroxide
O=C(c1cccnc1)c1ccccc1Cl
o-chlorophenyl 3-pyridyl ketone
O=S(=O)(O)O
sulfuric acid
O=[N+]([O-])O
nitric acid
O=S(=O)(O)O
sulfuric acid

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONis added dropwise
  2. 2
    FiltrationFiltration
  3. 3
    Sonstigedrying

Vorschrift

To a mixture of o-chlorophenyl 3-pyridyl ketone (10.0 g, 0.460 mol) and concentrated sulfuric acid at 0° C. is added dropwise a mixture of 90% nitric acid (2.40 ml) and concentrated sulfuric acid (6.0 ml). The resultant mixture is stirred one hour at 0° C., poured onto ice and neutralized with 30% ammonium hydroxide. Filtration and drying affords the title compound as a solid (11.4 g, 94.2%) which is identified by mass spectral analysis.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06706663B2uspto-grants-2004_03