HCID 69905199, compound → HCID 69906382, compound

HRID 649831Notes

Reaction equation

HRID 649831 reaction equation
[Br:1][C:2]1([O:13][CH3:14])[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[C:4]([O:11][CH3:12])[CH2:3]1>C(O)(=O)C.C(O)C.[Fe]>[Br:1][C:2]1([O:13][CH3:14])[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([O:11][CH3:12])[CH2:3]1

Participants

5

Reactant 1

HCID 69905199HCID 69905199, compound

Product 1

HCID 69906382HCID 69906382, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 4bromo-2,4-dimethoxy-nitrobenzene (0.48 g) and iron powder (0.42 g) in acetic acid (10 mL) and ethanol (10 mL) is heated to 120° C. for approximately 5 hours. The mixture is then cooled, filtered, and concentrated under reduced pressure. Water is added and the mixture is cooled in an ice bath and neutralized with solid potassium carbonate and then extracted with dichloromethane. These organic extracts are washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, concentrated under reduced pressure, then chromatographed over silica gel (20% ethyl acetate in hexanes is used as the eluant) to provide the desired compound as an amber oil.

Workup

  1. temperatureThe mixture is then cooled
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. additionWater is added
  5. temperaturethe mixture is cooled in an ice bath
  6. extractionextracted with dichloromethane
  7. washThese organic extracts are washed with saturated aqueous sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customchromatographed over silica gel (20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b2e546d687364220807ad01b3764be49
Source dataset
uspto-grants-2001_08
Patent number
US06271236B1

Reaction notes

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