N-(2-methoxyethyl)-N-methyl-4-nitrobenzylamine → 4-{[(2-Methoxyethyl)methylamino]methyl}phenylamine

HRID 566138Notes

Reaction equation

HRID 566138 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)[CH3:6]>C(O)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=1)[CH3:6]

Participants

3

Reactant 1

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

Product 1

HCID 235074614-{[(2-Methoxyethyl)methylamino]methyl}phenylamineYield 66.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In acetic acid (100 ml) was dissolved N-(2-methoxyethyl)-N-methyl-4-nitrobenzylamine (5.9 g), and to the mixture was added reduced iron (7.5 g) little by little. The mixture was stirred at room temperature overnight, and the solvent was evaporated. To the residue was added ethyl acetate, and precipitates were filtered off. The filtrate was washed with sodium hydroxide solution, water and saturated brine, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated to give 4-((N-(2-methoxyethyl)-N-methylamino)methyl)aniline (3.4 g) as red oil.

Workup

  1. customthe solvent was evaporated
  2. additionTo the residue was added ethyl acetate
  3. customprecipitates
  4. filtrationwere filtered off
  5. washThe filtrate was washed with sodium hydroxide solution, water and saturated brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customUnder reduced pressure, the solvent was evaporated

Sources & evidence

ORD record
ord-cf5fe72536324a2990b0a1993d65aa7d
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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