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

HRID 1616208Notes

Reaction equation

HRID 1616208 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:18][NH2:19]>C(O)C.CO>[Cl:11][C:4]1[N:3]=[C:2]([NH:19][CH3:18])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

6

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 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

2,6-Dichloro-3-Nitropyridine (2.0 g, 10 mmol) and sodium carbonate (2.8 g, 26 mmol) were added to a round bottom flask under nitrogen, and suspended in ethanol (100 mL). 2M methylamine in methanol (7.8 mL) was then added and stirred at room temperature for 3 hours. The yellow solution was concentrated, and then redissolved in ethyl acetate followed by washing with sodium bicarbonate and brine. The organic phase was dried over sodium sulfate, filtered, and concentrated. The yellow solid was then redissolved in ethanol and recrystallized to give 6-chloro-N-methyl-3-nitropyridin-2-amine (1-1) as a yellow solid. MS (M+H)+: observed=188.0, calculated=188.6.

Workup

  1. concentrationThe yellow solution was concentrated
  2. dissolutionredissolved in ethyl acetate
  3. washby washing with sodium bicarbonate and brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe yellow solid was then redissolved in ethanol
  8. customrecrystallized

Sources & evidence

ORD record
ord-d8daa7efa34444f286d0d2ee23b9cd9a
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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