Dimethylamine → N,N-dimethyl-5-nitropyridin-2-amine

HRID 450177

Reaction equation

HRID 450177 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>[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 674DimethylamineHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 75707N,N-dimethyl-5-nitropyridin-2-amineYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 0.314 g (1.99 mmol) of 2-chloro-5-nitropyridine in MeOH (1 mL) was added 5 mL of dimethylamine (2M solution in MeOH) at 0° C. and the mixture was warmed to room temperature. The reaction mixture was concentrated and extracted with EtOAc. The organic layer was washed successively with sat. NaHCO3 solution and brine, dried (Na2SO4), and concentrated to give 0.313 g (94% yield) of 2-dimethylamino-5-nitropyridine as an orange powder: 1H NMR (CDCl3) δ9.06 (d, J=2.7 Hz, 1H), 8.20 (dd, J=9.5, 2.7 Hz, 1H), 6.46 (dd, J=9.5, 0.4 Hz, 1H), 3.23 (s, 6H); LCMS (APCI+) m/z: 168 (MH+, 100%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed successively with sat. NaHCO3 solution and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-504f0d6541004dee8daa2c596cc37001
Source dataset
uspto-grants-2013_07
Patent number
US08486939B2

Linked notes

Loading…