반응 #452425

반응 방정식

N-(4-fluorobenzoyl)-4-aminoaniline

sodium nitrite

→

title compound

수율 72.0%

N-(4-fluorobenzoyl)-4-aminophenylhydrazine

수율 72.0%

용매

hydrochloric acid

hydrochloric acid

water

반응 조건

후처리

1. 1
   workup.ADDITIONafter the addition
2. 2
   workup.STIRRINGThe resultant white paste was stirred vigorously for 1 hour
3. 3
   여과was then filtered under vacuum
4. 4
   기타The solid which formed
5. 5
   기타was then partitioned between ethyl acetate and 5N sodium hydroxide
6. 6
   기타the phases separated
7. 7
   추출the aqueous phase was extracted again with dichloromethane
8. 8
   건조dried over sodium sulfate
9. 9
   농축concentrated under reduced pressure

실험 절차

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.

출처