Sodium Carbonate → HCID 15480137, compound

HRID 1872781Notes

Reaction equation

HRID 1872781 reaction equation
[N+:1]([C:4]1[C:9]([CH2:10][CH3:11])=[C:8]([N+:12]([O-])=O)[CH:7]=[CH:6][C:5]=1[O:15][CH3:16])([O-:3])=[O:2].C(=O)([O-])[O-].[Na+].[Na+]>CO>[NH2:12][C:8]1[CH:7]=[CH:6][C:5]([O:15][CH3:16])=[C:4]([N+:1]([O-:3])=[O:2])[C:9]=1[CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 15480136HCID 15480136, compound

Product 1

HCID 15480137HCID 15480137, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 2,4-dinitro-3-ethylanisole (23.7 mmol) in methanol (200 mL) is treated with stannous chloride (83.0 mmol). A reflux condenser is attached and the mixture is heated with an oil bath to 45° C. for two hours. The mixture is cooled to room temperature and poured over a saturated sodium carbonate solution (300 mL). The mixture is extracted with methylene chloride (400 mL). The methylene chloride layer is dried over magnesium sulfate and concentrated under reduced pressure to yield the crude product. This material is purified by chromatography (silica gel, 30% ethyl acetate/hexanes) to afford 4-amino-3-ethyl-2-nitroanisole.

Workup

  1. customA reflux condenser is attached
  2. temperatureThe mixture is cooled to room temperature
  3. extractionThe mixture is extracted with methylene chloride (400 mL)
  4. dry with materialThe methylene chloride layer is dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto yield the crude product
  7. customThis material is purified by chromatography (silica gel, 30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-64930424a1ec45dcaeaaf8ef83a9c778
Source dataset
uspto-grants-2000_08
Patent number
US06110952

Reaction notes

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