(4-Fluorophenyl)hydrazine → 5-Amino-4-(3-iodobenzoyl)-1-(4-fluorophenyl)pyrazole

HRID 429380

Reaction equation

HRID 429380 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.[I:10][C:11]1[CH:12]=[C:13]([CH:27]=[CH:28][CH:29]=1)[C:14]([C:16](=[CH:19]NC1C=CC=CC=1)[C:17]#[N:18])=[O:15]>C(O)C.CCCCCC>[NH2:18][C:17]1[N:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:9]=[CH:19][C:16]=1[C:14](=[O:15])[C:13]1[CH:27]=[CH:28][CH:29]=[C:11]([I:10])[CH:12]=1

Participants

5

Reactant 2

HCID 69982(4-Fluorophenyl)hydrazineHCID 670242742-(3-Iodobenzoyl)-3-phenylaminoacrylonitrile

Product 1

HCID 98660755-Amino-4-(3-iodobenzoyl)-1-(4-fluorophenyl)pyrazoleYield 87.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Procedure

A mixture of 4-fluorophenylhydrazine (26.6 g, 211 mmol) and 2-(3-iodobenzoyl)-3-phenylaminoacrylonitrile (79 g, 211 mmol) in ethanol (400 ml) was heated at reflux under a nitrogen atmosphere. After 30 minutes, the reaction mixture was cooled to room temperature, diluted with hexane to give 5-amino-4-(3-iodobenzoyl)-1-(4-fluorophenyl)pyrazole (75.1 g) as a solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere

Sources & evidence

ORD record
ord-d644431170b342c6b2d873d00690d2d2
Source dataset
uspto-grants-2001_11
Patent number
US06316466B1

Linked notes

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