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

HRID 629855Notes

Reaction equation

HRID 629855 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].CO>C(O)C>[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 4

HCID 887MethanolHCID 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

2,6-Dichloro-3-nitropyridine (2.0 g, 10.4 mmol) and sodium carbonate 2.75 g, 25.9 mmol) were added to a round bottom flask under nitrogen, and suspended in ethanol (100 mL). Methylamine in methanol (7.8 mL, 15.6 mmol, 2M) was then added and stirred at room temperature for 3 hours. The yellow solution was concentrated, and then re-dissolved 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 re-dissolved in ethanol and recrystallized to give 6-chloro-N-methyl-3-nitropyridin-2-amine (1-1) as a yellow solid. MS m/z (M+H): calculated=188.0228, calculated=188.0221.

Workup

  1. concentrationThe yellow solution was concentrated
  2. dissolutionre-dissolved 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 re-dissolved in ethanol
  8. customrecrystallized

Sources & evidence

ORD record
ord-f3c625c0256d4411a6117f8f9e8499b0
Source dataset
uspto-grants-2016_04
Patent number
US09315518B2

Reaction notes

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