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

HRID 880493Notes

Reaction equation

HRID 880493 reaction equation
Br[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>C1(C)C=CC=CC=1>[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 782402-Bromo-5-nitropyridine

Product 1

HCID 3168235-Nitro-2-(1-pyrrolidinyl)pyridineYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-bromo-5-nitro pyridine (300 mg, 1.48 mmol) and pyrrolidine (313 mg, 4.41 mmol) in toluene (5 mL) was heated at 110° C. for 2 h. The reaction mixture was allowed to cool to ambient temperature, poured onto ice-water, and the organic layer was separated. The aqueous layer was extracted with ethyl acetate (3×5 mL). The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate, filtered and concentrated in vacuo to afford 5-nitro-2-pyrrolidin-1-yl-pyridine (250 mg, 88%) as a solid.

Workup

  1. temperatureto cool to ambient temperature
  2. additionpoured onto ice-water
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×5 mL)
  5. washThe combined organic layers were washed with water, brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0155b015631d4828a816360f4fc2e57b
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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