تفاعل #452425

معادلة التفاعل

N-(4-fluorobenzoyl)-4-aminoaniline

sodium nitrite

→

title compound

المردود 72.0%

N-(4-fluorobenzoyl)-4-aminophenylhydrazine

المردود 72.0%

المذيبات

hydrochloric acid

hydrochloric acid

water

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONafter the addition
2. 2
   workup.STIRRINGThe resultant white paste was stirred vigorously for 1 hour
3. 3
   ترشيحwas then filtered under vacuum
4. 4
   أخرىThe solid which formed
5. 5
   أخرىwas then partitioned between ethyl acetate and 5N sodium hydroxide
6. 6
   أخرىthe phases separated
7. 7
   استخلاصthe aqueous phase was extracted again with dichloromethane
8. 8
   تجفيفdried over sodium sulfate
9. 9
   تركيزconcentrated under reduced pressure

الإجراء التجريبي

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.

المصدر