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

HRID 365243노트

반응식

HRID 365243 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매2회HCID 962Water용매

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cbd6b1681cdc489e9f8649ab85da9cee
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06126932

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