Реакция #811384

Уравнение реакции

N-Ethyldiisopropylamine

methylamine

6-Bromo-2-naphthoic acid

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

1-hydroxy-1H-benzotriazole monohydrate

→

title compound

Выход 95.6%

6-bromo-N-methyl-2-naphthamide

Выход 95.6%

Растворители

water

THF

dimethylformamide

Условия реакции

Обработка

1. 1
   Температураcooling
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 18 h
3. 3
   workup.STIRRINGwith stirring
4. 4
   Фильтрацияthe precipitate was collected by filtration
5. 5
   ПромывкаThe precipitate was washed successively with water and diisopropyl ether
6. 6
   Сушкаdried in the presence of phosphorus pentaoxide at 70° C.

Методика

6-Bromo-2-naphthoic acid (60.26 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (55.21 g) and 1-hydroxy-1H-benzotriazole monohydrate (44.1 g) were dissolved in dimethylformamide (960 ml) under an argon atmosphere. N-Ethyldiisopropylamine (37.23 g) was added with stirring under ice-cooling. A solution (2M; 192 ml) of methylamine in THF was added and the mixture was stirred at room temperature for 18 h. The reaction mixture was poured into water (8 L) with stirring and the precipitate was collected by filtration. The precipitate was washed successively with water and diisopropyl ether, and dried in the presence of phosphorus pentaoxide at 70° C. to give the title compound (60.6 g) as a crystalline powder.

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