반응 #41718

반응 방정식

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

용매

dimethylformamide

반응 조건

후처리

1. 1
   농축The reaction mixture was then concentrated
2. 2
   기타partitioned between ethyl acetate and water
3. 3
   기타The organic layer was separated
4. 4
   세척washed with brine
5. 5
   기타dried
6. 6
   여과filtered
7. 7
   농축concentrated in vacuum
8. 8
   기타to give brown solid
9. 9
   기타Purification on silica gel (2% triethyl amine/50% ethyl acetate in hexane)

실험 절차

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.

출처