تفاعل #41718

معادلة التفاعل

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

المذيبات

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   تركيزThe reaction mixture was then concentrated
2. 2
   أخرىpartitioned between ethyl acetate and water
3. 3
   أخرىThe organic layer was separated
4. 4
   غسيلwashed with brine
5. 5
   أخرىdried
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated in vacuum
8. 8
   أخرىto give brown solid
9. 9
   أخرىPurification on silica gel (2% triethyl amine/50% ethyl acetate in hexane)

الإجراء التجريبي

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.

المصدر