Methanol → 2-Amino-6-methoxy-3-nitropyridine

HRID 1449486Notes

Reaction equation

HRID 1449486 reaction equation
[Na].[NH2:2][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[C:5](Cl)[N:4]=1.[CH3:13][OH:14]>>[NH2:2][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[C:5]([O:14][CH3:13])[N:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 5360545Sodium

Product 1

HCID 38524282-Amino-6-methoxy-3-nitropyridine

Procedure

1.65 g (0.0717 mol; 2 equivalents (eq)) of sodium are dissolved in 100 cm3 of methanol. 6.2 g (35.7 mmol) of 2-amino-6-chloro-3-nitropyridine are added and the solution is brought to reflux for 8h. The methanol is evaporated under reduced pressure and the residue is taken up in the minimum amount of water (20 cm3). The solution is extracted with 100 cm3 of ethyl ether. The ether phase is washed with water (20 cm3), separated by settling, dried over MgSO4, decolored with animal charcoal and evaporated on a rotary evaporator to give a 1 st crop. The aqueous phase is extracted under the same conditions with 2 times 50 cm3 of ethyl acetate, giving a 2nd and 3rd crop.

Workup

  1. temperatureto reflux for 8h
  2. customThe methanol is evaporated under reduced pressure
  3. extractionThe solution is extracted with 100 cm3 of ethyl ether
  4. washThe ether phase is washed with water (20 cm3)
  5. customseparated
  6. dry with materialdried over MgSO4
  7. customevaporated on a rotary evaporator
  8. customto give a 1 st crop
  9. extractionThe aqueous phase is extracted under the same conditions with 2 times 50 cm3 of ethyl acetate
  10. customgiving a 2nd and 3rd crop

Sources & evidence

ORD record
ord-7234b7a01c024bd299f70f325cff5b1e
Source dataset
uspto-grants-1997_02
Patent number
US05599812

Reaction notes

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