Реакция #452425

Уравнение реакции

N-(4-fluorobenzoyl)-4-aminoaniline

sodium nitrite

→

title compound

Выход 72.0%

N-(4-fluorobenzoyl)-4-aminophenylhydrazine

Выход 72.0%

Растворители

hydrochloric acid

hydrochloric acid

water

Условия реакции

Обработка

1. 1
   workup.ADDITIONafter the addition
2. 2
   workup.STIRRINGThe resultant white paste was stirred vigorously for 1 hour
3. 3
   Фильтрацияwas then filtered under vacuum
4. 4
   ДругоеThe solid which formed
5. 5
   Другоеwas then partitioned between ethyl acetate and 5N sodium hydroxide
6. 6
   Другоеthe phases separated
7. 7
   Экстракцияthe aqueous phase was extracted again with dichloromethane
8. 8
   Сушкаdried over sodium sulfate
9. 9
   Концентрированиеconcentrated under reduced pressure

Методика

To a stirred suspension of 5.0 gm (23.9 mMol) N-(4-fluorobenzoyl)-4-aminoaniline in 42 mL concentrated hydrochloric acid at 0° C. was added dropwise a solution of 1.65 gm (23.9 mMol) sodium nitrite in 30 mL water. The mixture was stirred for 10 minutes after the addition was complete and was then added dropwise to a solution of 19.6 gm (86.87 mMol) stannous chloride dihydrate in 40 mL concentrated hydrochloric acid at 0° C. The resultant white paste was stirred vigorously for 1 hour and was then filtered under vacuum. The solid which formed was then partitioned between ethyl acetate and 5N sodium hydroxide, the phases separated and the aqueous phase was extracted again with dichloromethane. The combined organic phases were combined, dried over sodium sulfate and concentrated under reduced pressure to give 3.8 gm (72%) of the title compound as a brown solid which is suitable for use in subsequent reactions without further purification.

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