反应 #452425

反应方程式

N-(4-fluorobenzoyl)-4-aminoaniline

sodium nitrite

→

title compound

收率 72.0%

N-(4-fluorobenzoyl)-4-aminophenylhydrazine

收率 72.0%

溶剂

hydrochloric acid

hydrochloric acid

water

反应条件

后处理

1. 1
   workup.ADDITIONafter the addition
2. 2
   workup.STIRRINGThe resultant white paste was stirred vigorously for 1 hour
3. 3
   过滤was then filtered under vacuum
4. 4
   其他The solid which formed
5. 5
   其他was then partitioned between ethyl acetate and 5N sodium hydroxide
6. 6
   其他the phases separated
7. 7
   萃取the aqueous phase was extracted again with dichloromethane
8. 8
   干燥dried over sodium sulfate
9. 9
   浓缩concentrated under reduced pressure

实验过程

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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