7-Bromo-1-nitronaphthalene → 7-Bromonaphthalen-1-amine

HRID 891960Notes

Reaction equation

HRID 891960 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([N+:12]([O-])=O)[CH:6]=[CH:7][CH:8]=2)[CH:3]=1>O.[Fe]>[NH2:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[C:2]([Br:1])[CH:11]=[CH:10]2

Participants

4

Reactant 1

HCID 8259507-Bromo-1-nitronaphthalene

Product 1

HCID 222402477-Bromonaphthalen-1-amineYield 62%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

To a suspension of iron powder (1.66 g) in 25 ml water and 25% HCL (1.7 ml) was added 2-bromo-8-nitro-naphthalene (2.15 g, 8.5 mmol) and the reaction mixture was refluxed for 2 hours. The aqueous phase was extracted with ethyl acetate to give the crude product. Chromatography on silica gel (hexane/ethyl acetate 1/9 to 2/3) afforded 1.17 g (62%) of the product as brown oil. MS: m/e=222.2 (M+).

Workup

  1. temperaturethe reaction mixture was refluxed for 2 hours
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. customto give the crude product

Sources & evidence

ORD record
ord-4b8b42d0b5e24b4091e51e9a905e330b
Source dataset
uspto-grants-2006_02
Patent number
US07005432B2

Reaction notes

Loading…