Potassium Carbonate → 6-Chloro-2-dimethylamino-3-nitropyridine

HRID 1825499Notes

Reaction equation

HRID 1825499 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-].[K+].[K+].[CH3:18][NH:19][CH3:20].O1CCCC1>O1CCCC1>[Cl:11][C:4]1[N:3]=[C:2]([N:19]([CH3:20])[CH3:18])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 852392,6-Dichloro-3-nitropyridineHCID 22320367Dimethylamine tetrahydrofuran

Product 1

HCID 217876256-Chloro-2-dimethylamino-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2,6-dichloro-3-nitropyridine (1.9 g, 10 mmole) and potassium carbonate (1.66 g, 12 mmole) in 30 ml of tetrahydrofuran was stirred at 0° C. for 5 min. A solution of dimethylamine/tetrahydrofuran (2 M, 6 ml, 12 mmole) was added dropwise to the reaction mixture over 40 min. After stirring for 5 min at 0° C., the mixture was warmed to room temperature and stirred overnight. The reaction mixture was filtered and the filtrate was collected and concentrated under reduced pressure. The crude product was purified by flash chromatography, eluting with 87% hexane: 13% ethyl acetate to give

Workup

  1. stirringAfter stirring for 5 min at 0° C.
  2. temperaturethe mixture was warmed to room temperature
  3. stirringstirred overnight
  4. filtrationThe reaction mixture was filtered
  5. customthe filtrate was collected
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography
  8. washeluting with 87% hexane
  9. custom13% ethyl acetate to give

Sources & evidence

ORD record
ord-2936f7651f68431881e6a2e522a9cc49
Source dataset
uspto-grants-2006_05
Patent number
US07045519B2

Reaction notes

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