反応 #452425

反応方程式

N-(4-fluorobenzoyl)-4-aminoaniline

sodium nitrite

→

title compound

収率 72.0%

N-(4-fluorobenzoyl)-4-aminophenylhydrazine

収率 72.0%

溶媒

hydrochloric acid

hydrochloric acid

water

反応条件

後処理

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

実験手順

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.

出典