HCID 23507503, compound → HCID 23507127, compound

HRID 2228319Notes

Reaction equation

HRID 2228319 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1)[CH2:6][CH2:7][O:8][CH3:9]>C(O)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=1)[CH2:6][CH2:7][O:8][CH3:9]

Participants

3

Reactant 1

HCID 23507503HCID 23507503, compound

Product 1

HCID 23507127HCID 23507127, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In acetic acid (200 ml) was dissolved N,N-bis(2-methoxyethyl)-4-nitrobenzylamine (10.5 g), and to the mixture was added reduced iron (11 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, and the residue was purified with silica gel column chromatography (ethyl acetate) to give 4-((N,N-bis(2-methoxyethyl)amino)-methyl)aniline (6.2 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
  8. customthe residue was purified with silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-c8822453dbb1479b95f2d293bb39080d
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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