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

HRID 1471022Notes

Reaction equation

HRID 1471022 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]>C(O)C.C(Cl)Cl>[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

5

Reactant 2

HCID 674DimethylamineHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 75707N,N-dimethyl-5-nitropyridin-2-amineYield 100.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 2-chloro-5-nitropyridine (5.0 g, 31.5 mmol) and 40% solution of Dimethylamine (10.66 g, 95 mmol) in ethanol (40 mL) was heated to 75° C. for 1 hour. The mixture was cooled to ambient temperature, diluted with CH2Cl2 and washed with saturated aqueous NaHCO3 (3×100 mL) and brine. The organic was dried (MgSO4), filtered and concentrated to afford 5.27 g (100%) of the title compound. MS (ESI) m/z 168 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. washwashed with saturated aqueous NaHCO3 (3×100 mL) and brine
  3. dry with materialThe organic was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0d1456a41d984d0d93b03cd84182a32a
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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