Cyclohexylamine → 2-Cyclohexylamino-5-nitropyridine

HRID 377107Notes

Reaction equation

HRID 377107 reaction equation
[H-].[Na+].[CH:3]1([NH2:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Cl[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][N:12]=1>O1CCCC1>[CH:3]1([NH:9][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][N:12]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 24758Sodium hydrideHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 2615382-Cyclohexylamino-5-nitropyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
22 °C

Procedure

Sodium hydride (60% dispersion in mineral oil, 1.99 g, 49.8 mmol) was washed 3× with hexanes then a solution of cyclohexylamine (3.8 mL, 33.2 mmol) dissolved in tetrahydrofuran (50 mL) was added. After stirring for 30 minutes at 22° C., 2-chloro-5-nitropyridine (5.00 g, 31.5 mmol) was added and the reaction mixture was heated to reflux for 3 hours. The solution was cooled to ambient temperature, quenched with saturated aqueous NH4Cl and concentrated in vacuo. The residue was redissolved in ethyl acetate then washed 2× with saturated NaHCO3, saturated NaCl, dried over anhydrous Na2SO4 and concentrated in vacuo. The product was recovered as a brown oil.

Workup

  1. additionwas added
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 3 hours
  4. temperatureThe solution was cooled to ambient temperature
  5. customquenched with saturated aqueous NH4Cl
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was redissolved in ethyl acetate
  8. washthen washed 2× with saturated NaHCO3, saturated NaCl
  9. dry with materialdried over anhydrous Na2SO4
  10. concentrationconcentrated in vacuo
  11. customThe product was recovered as a brown oil

Sources & evidence

ORD record
ord-84ff30d223814133b4b9fb28de9d58b9
Source dataset
uspto-grants-2000_02
Patent number
US06022884

Reaction notes

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