1-Fluoro-4-nitronaphthalene → 4-Fluoronaphthalen-1-amine

HRID 1490146Notes

Reaction equation

HRID 1490146 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N+:12]([O-])=O)=[CH:4][CH:3]=1>CCOC(C)=O.[Pd]>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH2:12])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 2617641-Fluoro-4-nitronaphthalene

Product 1

HCID 152494054-Fluoronaphthalen-1-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-Fluoro-1-nitro-naphthalene (1 g) was dissolved in EtOAc (20 mL) and placed into a hydrogenating flask containing Palladium on activated charcoal (10%, 0.3 g). The reaction mixture was hydrogenated at 50 psi for 5 hr. During the reaction, the pressure of the hydrogen dropped due to the consuming of the hydrogen, and it was brought back to 50 psi a few times. Finally, the reaction stopped when all the starting material was used. The resulting solution was 5 filtered through a pad of celite and washed with EtOAc (20 mL). The clear filtrate was concentrated and dried under vacuum to yield 4-Fluoro-1-aminonaphthalene.

Workup

  1. customplaced into a hydrogenating flask
  2. customDuring the reaction
  3. customthe pressure of the hydrogen dropped due to the consuming of the hydrogen, and it
  4. filtrationfiltered through a pad of celite
  5. washwashed with EtOAc (20 mL)
  6. concentrationThe clear filtrate was concentrated
  7. customdried under vacuum

Sources & evidence

ORD record
ord-d9aef45163fd42239cecb9ac888d2c0f
Source dataset
uspto-grants-1997_10
Patent number
US05681861

Reaction notes

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