تفاعل #42274

معادلة التفاعل

3-bromo-5-[(dipropylamino)carbonyl]benzoic acid

N-methylpyrrolidinone

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title compound

3-Cyano-5-[(dipropylamino)carbonyl]benzoic acid

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةat which time the mixture is cooled
2. 2
   أخرىpartitioned between ethyl acetate and hydrochloric acid (3N)
3. 3
   غسيلThe organic layer is washed twice more with hydrochloric acid (3N)
4. 4
   تجفيفThe organic layer is dried over magnesium sulfate
5. 5
   تركيزconcentrated under high vacuum

الإجراء التجريبي

A mixture of 3-bromo-5-[(dipropylamino)carbonyl]benzoic acid (PREPARATION 4, 0.596 g, 1.82 mmol) and copper nitrile (0.325 g, 3.63 mmol) in N-methylpyrrolidinone (1.5 mL) is stirred at 175 degrees C. for 2.5 hour, at which time the mixture is cooled and partitioned between ethyl acetate and hydrochloric acid (3N). The organic layer is washed twice more with hydrochloric acid (3N) and then twice more with saline which had been acidified with a small amount of hydrochloric acid (3N). The organic layer is dried over magnesium sulfate and concentrated under high vacuum to give the title compound, NMR (CDCl3) delta 0.80, 1.02, 1.60, 1.73, 3.17, 3.51, 7.90, 8.31 and 8.41; an aliquot is crystallized from ethyl ether/dichloromethane/hexane-IR (diffuse reflectance) 3017, 2970, 2937, 2898, 2877, 2473, 2432, 2350, 2318, 2236, 1721, 1608, 1588, 1206 and 1196 cm−1.

المصدر