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

HRID 429372Notes

Reaction equation

HRID 429372 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.[N+:10]([C:13]1[CH:14]=[C:15]([CH:29]=[CH:30][CH:31]=1)[C:16]([C:18](=[CH:21]NC1C=CC=CC=1)[C:19]#[N:20])=[O:17])([O-:12])=[O:11]>C(O)C>[NH2:20][C:19]1[N:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:9]=[CH:21][C:18]=1[C:16](=[O:17])[C:15]1[CH:29]=[CH:30][CH:31]=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=1

Participants

4

Reactant 2

HCID 69982(4-Fluorophenyl)hydrazineHCID 696860762-(3-Nitrobenzoyl)-3-phenylaminoacrylonitrile

Product 1

HCID 222627595-Amino-1-(4-fluorophenyl)-4-(3-nitrobenzoyl)pyrazoleYield 97.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-fluorophenylhydrazine (2.24 g, 15.57 mmol) and 2-(3-nitrobenzoyl)-3-phenylaminoacrylonitrile (4.15 g, 14.16 mmol) in ethanol (50 ml) was heated at reflux under nitrogen atmosphere. After 1 h, the reaction mixture was cooled to room temperature and stirred for an additional 3 h. The solid was filtered and dried to give 5-amino-1-(4-fluorophenyl)-4-(3-nitrobenzoyl)pyrazole (4.5 g) as a solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen atmosphere
  3. filtrationThe solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-41dcb53769f14ace99a568bc0d3e3e14
Source dataset
uspto-grants-2001_11
Patent number
US06316466B1

Reaction notes

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