Réaction #41718

Équation de réaction

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

Solvants

dimethylformamide

Conditions de réaction

Traitement

1. 1
   ConcentrationThe reaction mixture was then concentrated
2. 2
   Autrepartitioned between ethyl acetate and water
3. 3
   AutreThe organic layer was separated
4. 4
   Lavagewashed with brine
5. 5
   Autredried
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated in vacuum
8. 8
   Autreto give brown solid
9. 9
   AutrePurification on silica gel (2% triethyl amine/50% ethyl acetate in hexane)

Mode opératoire

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.

Source