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

HRID 2364836Notes

Reaction equation

HRID 2364836 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 h. The cooled solution was concentrated in vacuo and the residue partitioned between CH2Cl2 and 1M 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 1M NaOH
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-26c4a19fbb014444aec41cf6cda8e6fd
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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