4-Fluorophenylhydrazine hydrochloride → N-[(E)-(4-bromo-3-pyridinyl)methylideneamino]-4-fluoroaniline

HRID 559656

Reaction equation

HRID 559656 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]=O.Cl.[F:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][NH2:19])=[CH:14][CH:13]=1.C([O-])(=O)C.[Na+]>C(O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1/[CH:8]=[N:19]/[NH:18][C:15]1[CH:16]=[CH:17][C:12]([F:11])=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 517045Sodium AcetateHCID 111167404-Bromopyridine-3-carbaldehyde

Product 1

HCID 59278491N-[(E)-(4-bromo-3-pyridinyl)methylideneamino]-4-fluoroaniline

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent3×

Conditions

Temperature
50 °C

Procedure

To a solution of 4-bromopyridine-3-carbaldehyde (2.50 g, 13.4 mmol) in ethanol (25 mL) and water (5 mL) was added 4-fluorophenyhydrazine hydrochloride (2.38 g, 14.6 mmol) (mixture turned a deep red) followed by sodium acetate (3.7 g, 27 mmol) in 5 mL of water (mixture turned a bright yellow). The mixture was warmed at 50° C. for 30 minutes to afford an orange precipitate. The mixture was cooled and diluted with water (50 mL) and the solid was collected by filtration. The filter cake was washed with water and dried to afford N-[1-(4-bromopyridin-3-yl)-meth-(E)-ylidene]-N′-(4-fluorophenyl)-hydrazine.

Workup

  1. customto afford an orange precipitate
  2. temperatureThe mixture was cooled
  3. filtrationthe solid was collected by filtration
  4. washThe filter cake was washed with water
  5. customdried

Sources & evidence

ORD record
ord-6aa6ce2da6c14612bb46a03b6f325060
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Linked notes

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