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

HRID 515231Notes

Reaction equation

HRID 515231 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 mmol) and sodium carbonate (2.8 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, 16 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 (28-1) as a yellow solid. HRMS (M+H)+: observed=188.0216, 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-5226676b9fd348fbbb450437d684511c
Source dataset
uspto-grants-2015_08
Patent number
US09108937B2

Reaction notes

Loading…