2,3-Difluoro-6-nitro{[2-(tetrahydropyran-2-yl)oxypropyl]oxy}benzene → 2,3-Difluoro-6-amino-{[2-(tetrahydropyran-2-yl)oxypropyl]oxy}benzene

HRID 846327Notes

Reaction equation

HRID 846327 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([N+:9]([O-])=O)[C:3]=1[O:12][CH2:13][CH:14]([O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1)[CH3:15]>C(O)C.[Pd]>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([NH2:9])[C:3]=1[O:12][CH2:13][CH:14]([O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1)[CH3:15]

Participants

4

Reactant 1

HCID 146971782,3-Difluoro-6-nitro{[2-(tetrahydropyran-2-yl)oxypropyl]oxy}benzene

Product 1

HCID 146971812,3-Difluoro-6-amino-{[2-(tetrahydropyran-2-yl)oxypropyl]oxy}benzene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1.82 g of the compound obtained in Example 1 dissolved in 50 ml of ethanol was added 500 mg of 5% palladium on charcoal. Catalytic reduction was carried out under atmospheric pressure for about 1 hour. The catalyst was removed by filtration, and the solvent was removed under reduced pressure to yield the titled compound. This product was used in the next step without further purification.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8467683d78d14fd3b3739a1dc57497fc
Source dataset
uspto-grants-1992_08
Patent number
US05136059

Reaction notes

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