تفاعل #41763

معادلة التفاعل

dimethylformamide

5-fluoro-2-nitrophenylamine

Potassium bis(trimethylsilyl)amide

(3-hydroxyphenyl)-N-methylcarboxamide

Potassium carbonate

→

N-methyl{4-[3-(methylamino)-4-nitro-phenoxy](2-pyridyl))carboxamide

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

الإجراء التجريبي

The mixture containing 5-fluoro-2-nitrophenylamine (1 eq), Potassium bis(trimethylsilyl)amide (2 eq) was stirred in dimethylformamide for 2 hours at room temperature. To this mixture was added (3-hydroxyphenyl)-N-methylcarboxamide (1 eq) and Potassium carbonate (1.2 eq) and stirred at 90° C. for 16 h. 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 gave N-methyl{4-[3-(methylamino)-4-nitro-phenoxy](2-pyridyl))carboxamide. It was taken in methanol and hydrogenated with catalytic amount of 10% Pd/C to give {4-[4-amino-3-(methylamino)phenoxy](2-pyridyl)}-N-methylcarboxamide. MS: MH+=272.

المصدر