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

HRID 730568Notes

Reaction equation

HRID 730568 reaction equation
[CH3:1][O:2][CH:3]([O:17][CH3:18])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[C:6]=1[N+:14]([O-])=O>CO.[Pd]>[CH3:18][O:17][CH:3]([O:2][CH3:1])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[C:6]=1[NH2:14]

Participants

4

Reactant 1

HCID 578349721-(2,2-Dimethoxyethyl)-2,3-dinitrobenzene

Product 1

HCID 578350073-(2,2-Dimethoxyethyl)benzene-1,2-diamineYield 73.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-(2,2-Dimethoxy-ethyl)-2,3-dinitro-benzene (1.85 g, 7.19 mmol) was dissolved in 20 mL of MeOH and 90 mg of 10% by weight Pd/C was added. This mixture was stirred under 1 atmosphere of H2 for 14 hours at room temperature. The mixture was filtered over celite and purified by chromatography to afford 3-(2,2-dimethoxy-ethyl)-benzene-1,2-diamine (1.04 g, 73%). 1H NMR (CDCl3) δ 2.87 (2H, d, J=5.3 Hz), 3.37 (6H, s), 4.50 (1H, t, J=5.3 Hz), 7.60 (6.62-6.66, m, 3H).

Workup

  1. filtrationThe mixture was filtered over celite
  2. custompurified by chromatography

Sources & evidence

ORD record
ord-1a1b9747da3648e183e4b75e49bd2996
Source dataset
uspto-grants-2009_09
Patent number
US07582760B2

Reaction notes

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