Pyrrolidine → 5-Nitro-2-(1-pyrrolidinyl)pyridine

HRID 1411405Notes

Reaction equation

HRID 1411405 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1>CCO>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 3168235-Nitro-2-(1-pyrrolidinyl)pyridineYield 78.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a slurry of 2-chloro-5-nitropyridine (10 g, 63.1 mmol) in EtOH (100 mL) at room temperature was added pyrrolidine (15.72 mL, 189 mmol) and the mixture was heated at 70° C. for 18 hours. The cooled solution was concentrated in vacuo and the residue partitioned between CH2Cl2 and 1 M NaOH. The organic layer was dried (Na2SO4), filtered and solvent removed in vacuo to give title compound (9.52 g, 78%). MS (ESI) m/z 194 (M+H)+.

Workup

  1. concentrationThe cooled solution was concentrated in vacuo
  2. customthe residue partitioned between CH2Cl2 and 1 M NaOH
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-4789a14a453843169676e759bdd18d77
Source dataset
uspto-grants-2014_12
Patent number
US08921514B2

Reaction notes

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