6-Bromo-1-nitronaphthalen-2-amine → 6-Bromonaphthalene-1,2-diamine

HRID 1751627Notes

Reaction equation

HRID 1751627 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N+:12]([O-])=O)=[C:7]([NH2:15])[CH:6]=[CH:5]2>C(O)C.[Ni]>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH2:15])[C:8]=2[NH2:12])[CH:3]=1

Participants

4

Reactant 1

HCID 218071856-Bromo-1-nitronaphthalen-2-amine

Product 1

HCID 220970716-Bromonaphthalene-1,2-diamineYield 89.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 6-bromo-1-nitronaphthalen-2-amine (11.6 g, 43.4 mmol) in ethanol (430 mL) under argon was added Raney Nickel (˜5 g, NOTE: no effort was made to remove the water from the nickel). Hydrogen gas was bubbled through the reaction mixture for 2 minutes. The reaction was stirred under an atmosphere of hydrogen at room temperature. After 16 hours, the Raney Nickel was removed by filtration over Celite and rinsed with ethyl acetate. The filtrate was thoroughly concentrated to yield 6-bromonaphthalene-1,2-diamine (9.2 g, 88% yield).

Workup

  1. customto remove the water from the nickel)
  2. customHydrogen gas was bubbled through the reaction mixture for 2 minutes
  3. customthe Raney Nickel was removed by filtration over Celite
  4. washrinsed with ethyl acetate
  5. concentrationThe filtrate was thoroughly concentrated

Sources & evidence

ORD record
ord-b11ee7811d074a498a47252296fd488e
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

Loading…