Hydrazine hydrate (1:1) → 4-(3-Fluoropyridin-4-yl)aniline

HRID 1510237Notes

Reaction equation

HRID 1510237 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1.O.NN>C(O)C.Cl[Fe](Cl)Cl>[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 690819133-Fluoro-4-(4-nitrophenyl)pyridine

Product 1

HCID 690819074-(3-Fluoropyridin-4-yl)anilineYield 70.7%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 702EthanolSolvent

Procedure

To a refluxing mixture of 3-fluoro-4-(4-nitrophenyl)pyridine (2.23 g), trichloroiron (130 mg) and activated carbon (1.12 g, 50 wt % of the starting material) in ethanol (74 mL) was added dropwise hydrazine hydrate (1.6 g), and the mixture was stirred for 3 hours. The insoluble materials were removed by filtration in hot and washed with ethanol. Most of ethanol was removed in vacuo, and to the residue was added water. Resulting solid was collected by filtration, and purified by column chromatography on silica gel eluting with hexane/ethyl acetate (1:2) to afford 4-(3-fluoropyridin-4-yl)aniline (1.36 g) a pale orange solid.

Workup

  1. customThe insoluble materials were removed by filtration in hot and
  2. washwashed with ethanol
  3. customMost of ethanol was removed in vacuo
  4. additionto the residue was added water
  5. customResulting solid
  6. filtrationwas collected by filtration
  7. custompurified by column chromatography on silica gel eluting with hexane/ethyl acetate (1:2)

Sources & evidence

ORD record
ord-b9434d01266c483dad4bebf1b35dc25f
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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