Ammonia → 6-Bromopyridine-2-carboxamide

HRID 29262

Reaktionsgleichung

Reaktionsgleichung von HRID 29262
[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.[NH3:11]>S(Cl)(Cl)=O.O1CCOCC1>[Br:1][C:2]1[N:7]=[C:6]([C:8]([NH2:11])=[O:10])[CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 222AmmoniaHCID 5939196-Bromopyridine-2-carboxylic acid

Produkt 1

HCID 219614086-Bromopyridine-2-carboxamideAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24386Thionyl ChlorideLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

6-Bromopicolinic acid (1000 mg, 4.95 mmol) was suspended in thionyl chloride (15 mL) and heated at 70° C. for 5 h. The reaction was cooled to room temperature and the volatiles were condensed under reduced pressure. A solution of ammonia (2M in dioxane (15 mL) was added to the residue and then the solvents were removed under reduced pressure. The crude residue was purified by MPLC with a gradient of 0 to 20% MeOH/dichloromethane to give 6-Bromo-pyridine-2-carboxylic acid amide as a white powder (555 mg, 45%). MS ES (MH+=201.0/203.0).

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. customcondensed under reduced pressure
  3. customthe solvents were removed under reduced pressure
  4. customThe crude residue was purified by MPLC with a gradient of 0 to 20% MeOH/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-c44d8a796e344fa9ab518435508d9ef8
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420066B2

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