4-Fluorophenylhydrazine hydrochloride → N-[(E)-(3,5-dibromo-4-pyridinyl)methylideneamino]-4-fluoroaniline

HRID 559620Notes

Reaction equation

HRID 559620 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:10])[C:7]=1[CH:8]=O.Cl.[F:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][NH2:20])=[CH:15][CH:14]=1.C([O-])(=O)C.[Na+]>C(O)C.O>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:10])[C:7]=1/[CH:8]=[N:20]/[NH:19][C:16]1[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 517045Sodium AcetateHCID 27629983,5-Dibromo-4-pyridinecarboxaldehyde

Product 1

HCID 59278325N-[(E)-(3,5-dibromo-4-pyridinyl)methylideneamino]-4-fluoroaniline

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3,5-dibromo-4-pyridinecarboxaldehyde (30.0 g, 113 mmol) in ethanol (1200 mL) at reflux was added 4-fluorophenylhydrazine hydrochloride (20.0 g, 123 mmol) in several portions followed by a solution of sodium acetate (31.0 g, 228 mmol) in water (200 mL). The mixture turned from a deep red to a bright yellow and over time a yellow solid precipitated. After 20 minutes, the mixture was cooled, diluted with water (1000 mL) and the yellow solid was collected by filtration. The solid was washed with water and dried to afford N-[1-(3,5-dibromopyridin-4-yl)-meth-(E)-ylidene]-N′-(4-fluorophenyl)-hydrazine.

Workup

  1. customprecipitated
  2. temperaturethe mixture was cooled
  3. additiondiluted with water (1000 mL)
  4. filtrationthe yellow solid was collected by filtration
  5. washThe solid was washed with water
  6. customdried

Sources & evidence

ORD record
ord-ef34a876d42a46bcbd1ddbad3a097269
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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