Methane → 3-(4-Ethyl-2-methoxyphenoxy)pyridin-2-amine

HRID 626006Notes

Reaction equation

HRID 626006 reaction equation
[CH2:1]([C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[C:9]([N+:14]([O-])=O)=[N:10][CH:11]=[CH:12][CH:13]=2)=[C:5]([O:19][CH3:20])[CH:4]=1)[CH3:2].C.O.NN>CO>[CH2:1]([C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[C:9]([NH2:14])=[N:10][CH:11]=[CH:12][CH:13]=2)=[C:5]([O:19][CH3:20])[CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 297MethaneHCID 24654Hydrazine hydrate (1:1)HCID 591912683-(4-Ethyl-2-methoxyphenoxy)-2-nitropyridine

Product 1

HCID 591912963-(4-Ethyl-2-methoxyphenoxy)pyridin-2-amineYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 3-(4-ethyl-2-methoxyphenoxy)-2-nitropyridine (1.3 g, 4.7 mmol) in methanol (30 ml) were added anhydrous Ferric chloride (66 mg) and activated charcoal (66 mg). The resulting mixture was heated to reflux and Hydrazine hydrate (80%) (2 mL, 39 mmol) was added dropwise. The reaction was allowed to stir under reflux condition for 5 hours, then filtered through celite. The filtrate was concentrated under reduced pressure, taken in ethyl acetate (150 ml). The organic phase was washed with water followed by brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 1.11 g of the title compound, 100% yield.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux
  3. temperatureunder reflux condition for 5 hours
  4. filtrationfiltered through celite
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. washThe organic phase was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1991217d009945df8595efbffb1737d7
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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