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

HRID 1898303Notes

Reaction equation

HRID 1898303 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>C(O)C>[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 82.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-chloro-5-nitropyridine (5.0 g, 0.0315 mol) in ethanol, pyrrolidine (5.5 g, 0.094 mol) was added. The reaction mixture was refluxed for 4-5 h. Ethanol was removed under vacuum and was diluted with water. The reaction mixture was extracted with ethyl acetate and concentrated to afford 5.0 g of the desired product. 1HNMR (CDCl3): δ 2.09 (s, 4H), 3.47-3.71 (m, 4H), 6.34 (d, J=6.3 Hz, 1H), 8.18 (dd, J=1.8 Hz, 1.8 Hz, 1H), 9.05 (s, 1H); MS [M+H]+: 194.30

Workup

  1. temperatureThe reaction mixture was refluxed for 4-5 h
  2. customEthanol was removed under vacuum
  3. additionwas diluted with water
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7506f5c879534198a13d0888656fd112
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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