Reaction #452425

Reaction equation

N-(4-fluorobenzoyl)-4-aminoaniline

sodium nitrite

→

title compound

Yield 72.0%

N-(4-fluorobenzoyl)-4-aminophenylhydrazine

Yield 72.0%

Solvents

hydrochloric acid

hydrochloric acid

water

Conditions

Workup

1. 1
   workup.ADDITIONafter the addition
2. 2
   workup.STIRRINGThe resultant white paste was stirred vigorously for 1 hour
3. 3
   Filtrationwas then filtered under vacuum
4. 4
   OtherThe solid which formed
5. 5
   Otherwas then partitioned between ethyl acetate and 5N sodium hydroxide
6. 6
   Otherthe phases separated
7. 7
   Extractionthe aqueous phase was extracted again with dichloromethane
8. 8
   Dryingdried over sodium sulfate
9. 9
   Concentrationconcentrated under reduced pressure

Procedure

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.

Source