(4-Fluorophenyl)hydrazine → 5-Amino4-(3-bromobenzoyl)-1-(4-fluorophenyl)pyrazole

HRID 429351

Reaction equation

HRID 429351 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.[Br: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]([Br:10])[CH:12]=1

Participants

5

Reactant 2

HCID 69982(4-Fluorophenyl)hydrazineHCID 696866072-(3-Bromobenzoyl)-3-phenylaminoacrylonitrile

Product 1

HCID 114512375-Amino4-(3-bromobenzoyl)-1-(4-fluorophenyl)pyrazoleYield 87.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Procedure

A mixture of 4-fluorophenylhydrazine (4.25 g, 33.7 mmol) and 2-(3-bromobenzoyl)-3-phenylaminoacrylonitrile (10.0 g, 30.7 mmol) in ethanol (100 ml) was heated at reflux under a nitrogen atmosphere. After 4 h, the reaction mixture was cooled to room temperature, diluted with hexane to give 5-amino-4-(3-bromobenzoyl)-1-(4-fluorophenyl)pyrazole (9.7 g) as a solid.

Workup

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

Sources & evidence

ORD record
ord-07974c9c1166473eb7542e6fc5c67129
Source dataset
uspto-grants-2001_11
Patent number
US06316466B1

Linked notes

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