Pyrrolidine → 4-Nitro-2-(pyrrolidin-1-yl)pyridine

HRID 602384

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][N:3]=1.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1>C1COCC1>[N+:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:7]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 80 °C

Procedure

2-Chloro-4-nitropyridine (2.0 g, 12.2 mmol) was dissolved in THF (30 mL) and the solution was added with pyrrolidine (3.25 mL, 38.9 mmol), followed by stirring at 80° C. overnight. After an insoluble matter of the reaction mixture was filtered off, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80) to obtain 4-nitro-2-(pyrrolidin-1-yl)pyridine (560 mg, 24%).

Workup

filtrationAfter an insoluble matter of the reaction mixture was filtered off
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80)

Sources & evidence

ORD record: ord-eecdad9079164c198f941dc04bb20403
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906522B2

Linked notes

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