(2-Nitrophenyl)hydrazine → 3-Chloro-5-(trifluoromethyl)-2-pyridinecarbaldehyde 2-(2-nitrophenyl)hydrazone

HRID 495395

Reaction equation

HRID 495395 reaction equation
[Cl:1][C:2]1[C:3]([CH:12]=O)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23][NH2:24])([O-:16])=[O:15]>C(O)C>[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23][N:24]=[CH:12][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][N:4]=1)([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 3314739(2-Nitrophenyl)hydrazineHCID 220187903-Chloro-5-(trifluoromethyl)picolinaldehyde

Product 1

HCID 686150543-Chloro-5-(trifluoromethyl)-2-pyridinecarbaldehyde 2-(2-nitrophenyl)hydrazone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-chloro-5-(trifluoromethyl)pyridine-2-carboxaldehyde (1.05 g) and 2-nitrophenylhydrazine (0.76 g) in ethanol (75 ml) was heated at reflux for 2.5 hours and then allowed to cool to room temperature overnight. The resulting orange solid was isolated by filtration and recrystallised (petrol) to afford the title compound as admixture of isomers, m.p. 127-35° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. customThe resulting orange solid was isolated by filtration
  4. customrecrystallised (petrol)

Sources & evidence

ORD record
ord-35658f78fa5c461cbe8d5acfc759eb93
Source dataset
uspto-grants-2005_09
Patent number
US06939882B1

Linked notes

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