Water → 6-Methoxy-N-methyl-3-nitropyridin-2-amine

HRID 55511Notes

Reaction equation

HRID 55511 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[N:10]=[C:9]([NH:11][CH3:12])[C:8]([N+:13]([O-:15])=[O:14])=[CH:7][CH:6]=1.O>CO>[CH3:1][O:2][C:5]1[N:10]=[C:9]([NH:11][CH3:12])[C:8]([N+:13]([O-:15])=[O:14])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 107500946-chloro-N-methyl-3-nitropyridin-2-amineHCID 10942334Sodium Methoxide

Product 1

HCID 30239146-Methoxy-N-methyl-3-nitropyridin-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

19 ml of a 28% methanolic solution of sodium methoxide were added dropwise to a solution of 6.00 g of 6-chloro-2-methylamino-3-nitropyridine (prepared as described in Preparation 66) in 120 ml of methanol at room temperature, and the resulting mixture was stirred at room temperature for 3 hours. At the end of this time, the reaction mixture was poured into water, after which it was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue was crystallized by trituration with ethanol, to give 5.34 g of the title compound, melting at 152°-153° C.

Workup

  1. extractionafter which it was extracted with ethyl acetate
  2. washThe extract was washed with an aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customafter which the solvent was removed by distillation under reduced pressure
  5. customThe residue was crystallized by trituration with ethanol

Sources & evidence

ORD record
ord-22168e8006dd4abcb9655250a75b343d
Source dataset
uspto-grants-1997_04
Patent number
US05624935

Reaction notes

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