Ethanol → 4,5-Dimethoxy-2-nitroaniline

HRID 1745914Notes

Reaction equation

HRID 1745914 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([N+:11]([O-:13])=[O:12])=[C:5]([N+:14]([O-])=O)[CH:4]=1.CCO>[Fe].O>[CH3:10][O:9][C:8]1[C:3]([O:2][CH3:1])=[CH:4][C:5]([NH2:14])=[C:6]([N+:11]([O-:13])=[O:12])[CH:7]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 2229891,2-Dimethoxy-4,5-dinitrobenzene

Product 1

HCID 46531524,5-Dimethoxy-2-nitroanilineYield 119.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

4.50 g (20.0 mmol) 4,5-dimethoxy-1,2-dinitrobenzene was taken into 50.0 mL EtOH/8.4 mL AcOH mixture. To this was added 4.00 g powdered iron (O). The reaction was heated to an oil bath temperature of 70° C. overnight. The reaction was allowed to cool to room temperature and was poured into 400 mL H2O. Aqueous layer was extracted several times with diethyl ether. Organic layers were dried over magnesium sulfate and evaporated under reduced pressure to give 4.73 g orange solid as a mixture of starting material and product. This solid was purified over silica gel (30% DCM in hexanes) to give the title compound 86A as an orange solid (1.15 g, 5.80 mmol).

Workup

  1. additionTo this was added 4.00 g
  2. temperatureto cool to room temperature
  3. extractionAqueous layer was extracted several times with diethyl ether
  4. dry with materialOrganic layers were dried over magnesium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f7894d8e5a5e45aa96d7481853c32e55
Source dataset
uspto-grants-2006_03
Patent number
US07019147B1

Reaction notes

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