Methane → HCID 59191421, compound

HRID 626040Notes

Reaction equation

HRID 626040 reaction equation
[CH2:1]([C:4]1[CH:19]=[CH:18][C:7]([O:8][C:9]2[C:10]([N+:15]([O-])=O)=[N:11][CH:12]=[CH:13][CH:14]=2)=[C:6]([O:20][CH3:21])[CH:5]=1)[CH2:2][CH3:3].C.O.NN>CO>[CH3:21][O:20][C:6]1[CH:5]=[C:4]([CH2:1][CH2:2][CH3:3])[CH:19]=[CH:18][C:7]=1[O:8][C:9]1[C:10]([NH2:15])=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 24654Hydrazine hydrate (1:1)HCID 59191383HCID 59191383, compound

Product 1

HCID 59191421HCID 59191421, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 3-(4-propyl-2-methoxyphenoxy)-2-nitropyridine (1.1 g, 3.8 mmol) in methanol (15 ml) was added anhydrous Ferric chloride (55 mg, 5% by wt) and activated charcoal (55 mg, 5% by wt). The resulting mixture was heated to reflux and hydrazine hydrate (570 mg, 11.45 mmol) was added dropwise. The reaction was allowed to stir under reflux condition overnight, then filtered through celite. The filtrate was concentrated under reduced pressure, taken in ethyl acetate (150 ml). The organic layer was washed with water followed by brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was passed through silica column (eluant ethylacetate/pet ether 1:3 to get 900 mg (91.3%) of title compound as a pale yellow solid.

Workup

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

Sources & evidence

ORD record
ord-35b4589fdf8b4ccd87ae792e7ab153c4
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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