Methylamine → 6-chloro-N-methyl-3-nitropyridin-2-amine

HRID 1738245Notes

Reaction equation

HRID 1738245 reaction equation
[CH3:1][NH2:2].Cl[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([Cl:13])[N:5]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Cl:13][C:6]1[N:5]=[C:4]([NH:2][CH3:1])[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 10340Sodium CarbonateHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 107500946-chloro-N-methyl-3-nitropyridin-2-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20.0 ml of a 30% ethanolic solution of methylamine were added dropwise to a mixture of 29.0 g of 2,6-dichloro-3-nitropyridine, 300 ml of ethanol and 36.6 g of sodium carbonate, whilst cooling with ice, and the resulting mixture was stirred at room temperature for 8 hours. At the end of this time, the reaction mixture was freed from ethanol by distillation. The residue was diluted with 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 22.3 g of the title compound, melting at 114° C.

Workup

  1. temperaturewhilst cooling with ice
  2. distillationAt the end of this time, the reaction mixture was freed from ethanol by distillation
  3. additionThe residue was diluted with water
  4. extractionafter which it was extracted with ethyl acetate
  5. washThe extract was washed with an aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customafter which the solvent was removed by distillation under reduced pressure
  8. customThe residue was crystallized by trituration with ethanol

Sources & evidence

ORD record
ord-996ae191a8c349d2953a6d7bd0eec33e
Source dataset
uspto-grants-1999_10
Patent number
US05962470

Reaction notes

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