Nitric Acid → 3-Nitro-5-(trifluoromethyl)pyridin-2-amine

HRID 53599

Reaktionsgleichung

Reaktionsgleichung von HRID 53599
OS(O)(=O)=O.[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][N:8]=1.[N+:17]([O-])([OH:19])=[O:18].[OH-].[Na+]>>[NH2:6][C:7]1[C:12]([N+:17]([O-:19])=[O:18])=[CH:11][C:10]([C:13]([F:14])([F:16])[F:15])=[CH:9][N:8]=1

Komponenten

5

Edukt 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 7358622-Amino-5-(trifluoromethyl)pyridine

Produkt 1

HCID 106083913-Nitro-5-(trifluoromethyl)pyridin-2-amineAusbeute 247 %

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To ice-water bath cooled, conc. H2SO4 (10 mL) was added 2-amino-5-trifluoromethylpyridine (1.70 g, 10.5 mmol). The resulting solution was heated to 50° C. and 69-71% HNO3 (1.7 mL, 2.6 mmol) was added dropwise over 10 min with stirring. The resulting solution was stirred at 80° C. for 46 h, then allowed to cool to room temperature, poured into ice-water (100 mL) and basified to pH 9 with 40% aq NaOH. The resulting mixture was extracted with EtOAc (5×40 mL). The EtOAc solution was dried (MgSO4), and evaporated to give 1.33 g (61%) of 50 as a yellow powder, mp 191°-3° C. 1H NMR (CDCl3), 6.140 (bs, 1H), 7.916 (bs, 1H), 8.590 (s, 1H), 8.670 (s, 1H).

Aufarbeitung

  1. temperatureTo ice-water bath cooled
  2. stirringThe resulting solution was stirred at 80° C. for 46 h
  3. temperatureto cool to room temperature
  4. extractionThe resulting mixture was extracted with EtOAc (5×40 mL)
  5. dry with materialThe EtOAc solution was dried (MgSO4)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-14df21c5ef1e46c3b34e1458bcb34cfa
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05620978

Verknüpfte Notizen

Wird geladen…