Reaktion #41718

Reaktionsgleichung

4-amino-3-nitrophenol

potassium bis(trimethylsilyl)amide

(4-chloro(2-pyridyl))-N-methylcarboxamide

potassium carbonate

→

4-[(4-amino-3-nitrophenyl)oxy]-N-methylpyridine-2-carboxamide

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was then concentrated
2. 2
   Sonstigepartitioned between ethyl acetate and water
3. 3
   SonstigeThe organic layer was separated
4. 4
   Waschenwashed with brine
5. 5
   Sonstigedried
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuum
8. 8
   Sonstigeto give brown solid
9. 9
   SonstigePurification on silica gel (2% triethyl amine/50% ethyl acetate in hexane)

Vorschrift

A mixture containing 4-amino-3-nitrophenol (1 eq) and potassium bis(trimethylsilyl)amide (2 eq) was stirred in dimethylformamide for 2 hours at room temperature. To this mixture was added (4-chloro(2-pyridyl))-N-methylcarboxamide (1 eq) and potassium carbonate (1.2 eq) and stirred at 90° C. for 3 days. The reaction mixture was then concentrated and partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, dried, filtered, and concentrated in vacuum to give brown solid. Purification on silica gel (2% triethyl amine/50% ethyl acetate in hexane) gave 4-[(4-amino-3-nitrophenyl)oxy]-N-methylpyridine-2-carboxamide as an orange solid. The product gave satisfactory NMR. HPLC, 3.39 min; MS: MH+=289.

Quelle