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

HRID 1361154Notes

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

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

customto afford an orange precipitate
temperatureThe mixture was cooled
filtrationthe solid was collected by filtration
washThe filter cake was washed with water
customdried

Sources & evidence

ORD record: ord-e74a92ec70f84243a96a0b1ddebf1485
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879873B2

Reaction notes

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