N-(2-Methoxyethyl)-2-nitroaniline → 1-N-(2-methoxyethyl)benzene-1,2-diamine

HRID 1096655Notes

Reaction equation

HRID 1096655 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O>CO.C(O)(=O)C.[Zn]>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]1[C:7]([NH2:12])=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 1

HCID 10375425N-(2-Methoxyethyl)-2-nitroaniline

Product 1

HCID 102614521-N-(2-methoxyethyl)benzene-1,2-diamineYield 72%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

The residue 109A was dissolved in methanol (60 mL) and acetic acid (4 mL). Zinc metal (3.24 g, 49.6 mmol) was added and the mixture was stirred overnight at room temperature. The reaction was decanted off from unreacted zinc metal. The solvent was removed under vacuum and resuspended in ethyl acetate (30 mL). The precipitate was removed by filtration on a Buchner funnel with Celite. Solvent was removed from the filtrate and the residue was purified by column chromatography (2% MeOH/DCM) to give the product N1-(2-methoxyethyl)benzene-1,2-diamine (109B) as a red oil (422 mg, 72% yield over two steps). ESI-MS:m/z 167.4 (M+H)+.

Workup

  1. customThe reaction was decanted off from unreacted zinc metal
  2. customThe solvent was removed under vacuum
  3. customThe precipitate was removed by filtration on a Buchner funnel with Celite
  4. customSolvent was removed from the filtrate
  5. customthe residue was purified by column chromatography (2% MeOH/DCM)

Sources & evidence

ORD record
ord-46108410ddf843bca44d8d93e7125b22
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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