Cyclohexylamine → 2-Cyclohexylamino-5-nitropyridine

HRID 2271293Notes

Reaction equation

HRID 2271293 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 3x 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 2x 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 2x 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-f15677bedf89460ca19e28cbde3603bc
Source dataset
uspto-grants-2001_12
Patent number
US06333341B1

Reaction notes

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