HCID 69905199, compound → HCID 69906382, compound

HRID 1276222Notes

Reaction equation

HRID 1276222 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 4-bromo-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-3b4304c07c594297ab58305933cd6350
Source dataset
uspto-grants-2000_12
Patent number
US06166028

Reaction notes

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