5-Bromo-N-ethyl-2-nitroaniline → 5-broMo-N1-ethylbenzene-1,2-diaMine

HRID 2202858Notes

Reaction equation

HRID 2202858 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-])=O)=[C:6]([CH:10]=1)[NH:7][CH2:8][CH3:9]>CC(O)=O.[Zn]>[Br:1][C:2]1[CH:10]=[C:6]([NH:7][CH2:8][CH3:9])[C:5]([NH2:11])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 249029765-Bromo-N-ethyl-2-nitroaniline

Product 1

HCID 592936595-broMo-N1-ethylbenzene-1,2-diaMineYield 45.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc (8.0 g) was added to a solution of 5-bromo-N-ethyl-2-nitroaniline (3.0 g) in AcOH (60 ml) at room temperature. The mixture was stirred at room temperature for 30 min. The insoluble material was removed by filtration, and the filtrate was concentrated in vacuo. The mixture was neutralized with saturated NaHCO3 solution at room temperature and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo to give the title compound (1.2 g) as a pale yellow solid.

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customwas neutralized with saturated NaHCO3 solution at room temperature
  4. extractionextracted with EtOAc
  5. customThe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-782fed728c9b457ab3b9a78bcd0d80b6
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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