Dimethylformamide → N-Methyl-3-nitro-2-pyridinamine

HRID 463547Notes

Reaction equation

HRID 463547 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:11][N:12](C)C=O>>[CH3:11][NH:12][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 556349N-Methyl-3-nitro-2-pyridinamineYield 80%

Procedure

25 g (0.16M) of 2-chloro-3-nitropyridine is dissolved in 200 ml dimethylformamide. For three hours monomethylamine is bubbled into the solution. The mixture is heated to reflux overnight. After the solvent is removed the oily residue is triturated with water and the solid is collected and air dried. The crude material is recrystallized from hexane to give 19.5 g (80% yield) of title compound, melting point 62°-3° C.

Workup

  1. customFor three hours monomethylamine is bubbled into the solution
  2. temperatureThe mixture is heated
  3. temperatureto reflux overnight
  4. customAfter the solvent is removed the oily residue
  5. customis triturated with water
  6. customthe solid is collected
  7. customair dried
  8. customThe crude material is recrystallized from hexane

Sources & evidence

ORD record
ord-a608ea0466354118bdde3e3f6d659f10
Source dataset
uspto-grants-1985_05
Patent number
US04520196

Reaction notes

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