반응 #42274

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

N-methylpyrrolidinone

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title compound

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

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후처리

1. 1
   온도at which time the mixture is cooled
2. 2
   기타partitioned between ethyl acetate and hydrochloric acid (3N)
3. 3
   세척The organic layer is washed twice more with hydrochloric acid (3N)
4. 4
   건조The organic layer is dried over magnesium sulfate
5. 5
   농축concentrated under high vacuum

실험 절차

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.

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