1-(Benzyloxy)-2,3-dinitrobenzene → 3-(Benzyloxy)benzene-1,2-diamine

HRID 1030520Notes

Reaction equation

HRID 1030520 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([N+:18]([O-])=O)=[C:11]([N+:15]([O-])=O)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)C.[Ni]>[CH2:1]([O:8][C:9]1[C:10]([NH2:18])=[C:11]([NH2:15])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 139713581-(Benzyloxy)-2,3-dinitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 44012883-(Benzyloxy)benzene-1,2-diamineYield 102.3%

Reagents, catalysts & solvents 1

HCID 86745698ethanol Raney-nickelSolvent

Procedure

To a solution of 3-benzyloxy-1,2-dinitrobenzene (2 g, 0.0073 mol) in 300 ml ethanol Raney-nickel (1 g) was added and the mixture was hydrogenated at room temperature and atmospheric pressure until the uptake of hydrogen ceased (30 min). The colourless solution was filtered (celite) and evaporated to dryness in vacuo to give the title compound as an unstable oil (1.6 g) which was used immediately for the next step.

Workup

  1. customwas hydrogenated at room temperature
  2. custom(30 min)
  3. filtrationThe colourless solution was filtered (celite)
  4. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-c18ccd15a23a4d11834ee6c982afc680
Source dataset
uspto-grants-1992_04
Patent number
US05106862

Reaction notes

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