Pyrrolidine → 3-Methoxy-5-nitro-2-(pyrrolidin-1-yl)pyridine

HRID 506506Notes

Reaction equation

HRID 506506 reaction equation
Cl[C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([N+:10]([O-:12])=[O:11])=[CH:4][N:3]=1.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>CN(C)C=O>[CH3:9][O:8][C:7]1[C:2]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[N:3][CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[CH:6]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 234561522-Chloro-3-methoxy-5-nitropyridine

Product 1

HCID 574315163-Methoxy-5-nitro-2-(pyrrolidin-1-yl)pyridineYield 97.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3 g (15.91 mmol) of 2-chloro-3-methoxy-5-nitropyridine and 2 ml (23.86 mmol) of pyrrolidine in 30 ml of dimethylformamide is heated at 100° C. for 4 hours. The reaction mixture is subsequently concentrated under reduced pressure and then taken up in 100 ml of water and extracted three times with 100 ml of ethyl acetate. The organic phases are combined, then washed twice with 50 ml of water then once with 50 ml of a saturated sodium chloride solution, dried over sodium sulfate and then concentrated under reduced pressure. 3.47 g of the expected compound are thus isolated in the form of an orangey powder.

Workup

  1. concentrationThe reaction mixture is subsequently concentrated under reduced pressure
  2. extractionextracted three times with 100 ml of ethyl acetate
  3. washwashed twice with 50 ml of water
  4. dry with materialonce with 50 ml of a saturated sodium chloride solution, dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bd838836a6014061ab81a8e94dc27ee5
Source dataset
uspto-grants-2010_08
Patent number
US07786104B2

Reaction notes

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