Tetrahydrofuran → 4-(Pyridin-2-yl)aniline

HRID 1592812Notes

Reaction equation

HRID 1592812 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:6][CH:5]=1)([O-])=O.C1COCC1.NN>[Pd].C(O)C>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:7]1[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 9321HydrazineHCID 4595562-(4-Nitrophenyl)pyridine

Product 1

HCID 4595184-(Pyridin-2-yl)anilineYield 69.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(4-Nitrophenyl)pyridine (1.10 g) and 10% Pd/C (300 mg) were dissolved suspended in 80 mL of an 8:1 solution of 30 mL of THF and 10 mL of ethanol under an atmosphere of dry N2. To this solution was added 1.0 mL of anhydrous hydrazine. The reaction mixture was stirred at room temperature overnight and then filtered. The filtrate was concentrated under vacuum. The residue was partitioned between dichloromethane and water and the organic layer was washed with brine, dried over MgSO4, filtered and concentrated under vacuum. The residue was purified via silica gel chromatography to give 653.3 mg of 4-(pyridin-2-yl)benzenamine.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under vacuum
  3. customThe residue was partitioned between dichloromethane and water
  4. washthe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified via silica gel chromatography

Sources & evidence

ORD record
ord-77713664e9da410d99a79c6a1d7f73e9
Source dataset
uspto-grants-2007_11
Patent number
US07294616B2

Reaction notes

Loading…