N-(4-Aminophenyl)-4-fluorobenzamide → N-(4-fluorobenzoyl)-4-aminophenylhydrazine

HRID 843968Notes

Reaction equation

HRID 843968 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[N:18]([O-])=O.[Na+]>Cl.O>[F:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([N:8]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[NH2:18])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 10988055N-(4-Aminophenyl)-4-fluorobenzamideHCID 23668193Sodium Nitrite

Product 1

HCID 22611296N-(4-fluorobenzoyl)-4-aminophenylhydrazineYield 72%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

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.

Workup

  1. additionafter the addition
  2. stirringThe resultant white paste was stirred vigorously for 1 hour
  3. filtrationwas then filtered under vacuum
  4. customThe solid which formed
  5. customwas then partitioned between ethyl acetate and 5N sodium hydroxide
  6. customthe phases separated
  7. extractionthe aqueous phase was extracted again with dichloromethane
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5b8ffbce509b474682d98007da54fdad
Source dataset
uspto-grants-2002_04
Patent number
US06380201B1

Reaction notes

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