Sulfuric Acid → 3-Benzyloxy-5-hydroxypyridine

HRID 1168947

Reaktionsgleichung

Reaktionsgleichung von HRID 1168947
[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11](N)[CH:12]=[N:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)[OH:17].N([O-])=O.[Na+].[OH-].[Na+].[Na+].[Cl-]>O>[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]([OH:17])[CH:12]=[N:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 5

HCID 1118Sulfuric Acid2×HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 229897355-(Benzyloxy)pyridin-3-amineHCID 23668193Sodium Nitrite

Produkt 1

HCID 229897043-Benzyloxy-5-hydroxypyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel3×

Versuchsvorschrift

The 5-(phenylmethoxy)-3-pyridylamine (1.61 g, 8.00 mmol) was stirred into concentrated sulfuric acid (1.7 mL), water (2.5 mL) and ice (4 g). This mixture was allowed to stir for 10 min until the solution became homogeneous. To this cold, stirring solution was added a solution of sodium nitrite (552 mg, 8.00 mmol) in water (2 mL). The mixture was allowed to stir for 10 min. A boiling solution of concentrated sulfuric acid (5 mL) and water (4 mL) was added. The mixture was heated until all solids dissolved. Ice was added to cool the reaction. The pH was adjusted to 8 with 10% NaOH solution and saturated NaCl solution was added. The product was extracted with ethyl acetate (4×100 mL). The combined ethyl acetate extracts were dried (Na2SO4), filtered, concentrated by rotary evaporation and briefly vacuum to give 1.52 g (94.4%).

Aufarbeitung

  1. stirringTo this cold, stirring solution
  2. stirringto stir for 10 min
  3. temperatureThe mixture was heated until all solids
  4. dissolutiondissolved
  5. additionIce was added
  6. temperatureto cool
  7. customthe reaction
  8. additionwas added
  9. extractionThe product was extracted with ethyl acetate (4×100 mL)
  10. dry with materialThe combined ethyl acetate extracts were dried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated by rotary evaporation and briefly vacuum
  13. customto give 1.52 g (94.4%)

Quellen und Nachweise

ORD-Eintrag
ord-0cc9d436252e46e9ae914c901114466e
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06627648B1

Verknüpfte Notizen

Wird geladen…