2-Chloro-5-nitropyridine → N,N-dimethyl-5-nitropyridin-2-amine

HRID 1668791Notes

Reaction equation

HRID 1668791 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][NH:12][CH3:13].CO>CO>[CH3:11][N:12]([CH3:13])[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 783082-Chloro-5-nitropyridineHCID 22497844Dimethylamine methanol

Product 1

HCID 75707N,N-dimethyl-5-nitropyridin-2-amineYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-chloro-5-nitropyridine (317.08 mg, 2 mmol) in 1 ml of methanol was added of 2 M dimethylamine/MeOH (5 ml, 10 mmol) in a sealed tube at 0° C. The reaction mixture was warmed up to room temperature and stirred over night. After evaporating the solvent, the residue was diluted with EtOAc (20 ml), washed with saturated NaHCO3 aq., brine, dried over Na2SO4, filtered and concentrated by vacuum, yielding 334 mg (100%) of yellow solids. 1H NMR (CDCl3): 9.06 (d, J=2.7 Hz, 1H), 8.22-8.18 (m, 1H), 6.46 (d, J=9.3 Hz, 1H), 3.23 (s, 6H).

Workup

  1. customAfter evaporating the solvent
  2. additionthe residue was diluted with EtOAc (20 ml)
  3. washwashed with saturated NaHCO3 aq., brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated by vacuum

Sources & evidence

ORD record
ord-a777f72d9ffe4f2e9cd9424718d992a6
Source dataset
uspto-grants-2011_08
Patent number
US07989462B2

Reaction notes

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