Sulfuric Acid → HCID 67485361, Verbindung

HRID 534014Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 534014
[Br:1][C:2]1[CH:3]=[C:4]([O:10][C:11]2[C:12]([CH3:17])=[N:13][CH:14]=[CH:15][CH:16]=2)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[OH:18]S(O)(=O)=O.[OH-].[Na+]>O>[Br:1][C:2]1[CH:3]=[C:4]([O:10][C:11]2[C:12]([CH3:17])=[N:13][CH:14]=[CH:15][CH:16]=2)[C:5]([C:8]([NH2:9])=[O:18])=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 67485726HCID 67485726, Verbindung

Produkt 1

HCID 67485361HCID 67485361, VerbindungAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

to 5-bromo-3-(2-methylpyridin-3-yloxy)picolinonitrile (15 g, 52 mmol) was added concentrated H2SO4 (30 mL) and the slurry was left to stir overnight, at which point the material was fully dissolved. The reaction was poured into 0° C. water in small portions. While maintaining the temp below 20° C., the aqueous layer was basified by the addition of NaOH pellets, to a pH of ˜5, at which point a solid formed. The solid was filtered and the remaining aqueous layer was extracted with EtOAc. The organic layers, combined with the solid, were washed with brine, dried over MgSO4 and concentrated in vacuo to yield 5-bromo-3-(2-methylpyridin-3-yloxy)picolinamide (11 g, 69%).

Aufarbeitung

  1. waitthe slurry was left
  2. dissolutionwas fully dissolved
  3. temperatureWhile maintaining the temp below 20° C.
  4. customformed
  5. filtrationThe solid was filtered
  6. extractionthe remaining aqueous layer was extracted with EtOAc
  7. washwere washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cca6953637194a588fcd825596faea73
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853409B2

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