Hydrazine → 4-{[(2-Methoxyethyl)methylamino]methyl}phenylamine

HRID 2236930Notes

Reaction equation

HRID 2236930 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1.NN>[Ni].CO>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=1)[CH3:16]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 23507717N-(2-methoxyethyl)-N-methyl-4-nitrobenzylamine

Product 1

HCID 235074614-{[(2-Methoxyethyl)methylamino]methyl}phenylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2-methoxy-ethyl)-methyl-(4-nitro-benzyl)-amine, from step 1, (56 mg, 0.25 mmol) is added methanol (1 mL), hydrazine (33 μL), and Raney-Nickel (10 mg). The reaction mixture is shaken at room temperature for 16 hours, then filtered and the solution concentrated to yield 4-{[(2-Methoxy-ethyl)-methyl-amino]-methyl}-phenylamine, which is used as such for the subsequent reaction.

Workup

  1. filtrationfiltered
  2. concentrationthe solution concentrated

Sources & evidence

ORD record
ord-eee4dc77e3a2439a97a0ed3ddeedfa1a
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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