Nitric Acid → 2-Amino-5-chloro-3-nitropyridine

HRID 53591

Reaktionsgleichung

Reaktionsgleichung von HRID 53591
OS(O)(=O)=O.[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1.[N+:14]([O-])([OH:16])=[O:15].[OH-].[Na+]>>[NH2:6][C:7]1[C:12]([N+:14]([O-:16])=[O:15])=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1

Komponenten

5

Edukt 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 661742-Amino-5-chloropyridine

Produkt 1

HCID 2241682-Amino-5-chloro-3-nitropyridineAusbeute 56 %

Versuchsvorschrift

To 150 mL of conc. H2SO4 was added 42.96 g (334 mmol) of 2-amino-5-chloropyridine in portions with stirring and cooling (ice-water bath). To the resulting solution was added dropwise 22.5 mL of 69-71% HNO3 (355 mmol) at 50° C. (at such a rate that maintain the temperature within 50°-55° C.) over 1 h. The resulting mixture was stirred at 60° C. for 3 h, poured into ice-water (about 1,500 mL) with stirring, then basified to pH 9 by the addition of 40% aq NaOH with stirring and cooling. The precipitate was filtered, washed with water (6×50 mL), and dried to give 32.47 g (56%) of 2 as a yellow powder, mp 190°-191° C. (lit. 191°-2° C. (Israel, M. & Day, A. R., J. Org. Chem. 24:1455-1460 (1959))). 1H NMR (DMSO-d6), 8.044-8.055 (m, 3H), 8.054 (d, 1H, J=3.9).

Aufarbeitung

  1. temperaturethat maintain the temperature within 50°-55° C.) over 1 h
  2. stirringThe resulting mixture was stirred at 60° C. for 3 h
  3. stirringwith stirring
  4. stirringwith stirring
  5. temperaturecooling
  6. filtrationThe precipitate was filtered
  7. washwashed with water (6×50 mL)
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-41cc4051fa274374b57a5cf8117f07b8
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05620978

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