4-(5-fluoro-2-nitrophenoxy)tetrahydro-2H-pyran → 4-Fluoro-2-(oxan-4-yloxy)aniline

HRID 240606Notes

Reaction equation

HRID 240606 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-])=O)=[C:6]([CH:14]=1)[O:7][CH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1>C(OC(=O)C)C.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:15])=[C:6]([O:7][CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:14]=1

Participants

4

Reactant 1

HCID 533521804-(5-fluoro-2-nitrophenoxy)tetrahydro-2H-pyran

Product 1

HCID 584130794-Fluoro-2-(oxan-4-yloxy)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-(5-Fluoro-2-nitrophenoxy)tetrahydro-2-H-pyran (8.4 g) was dissolved in ethylacetate (30 ml) and Pd/C (500 mg) was added. The reaction was hydrogenated at room temperature and 50 PSI. The mixture was concentrated in vacuo to give the intended product.

Workup

  1. customwas hydrogenated at room temperature
  2. concentrationThe mixture was concentrated in vacuo
  3. customto give the intended product

Sources & evidence

ORD record
ord-2cfdc8daddad4ec6982432969dae3fbe
Source dataset
uspto-grants-2014_02
Patent number
US08648068B2

Reaction notes

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