Potassium Carbonate → 5-Nitro-2-(1-pyrrolidinyl)pyridine

HRID 541220

Reaction equation

HRID 541220 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)([O-])[O-].[K+].[K+]>CC#N>[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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 3168235-Nitro-2-(1-pyrrolidinyl)pyridineYield 93.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-chloro-5-nitropyridine (1.58 g, 10.00 mmol, 1.00 equiv), pyrrolidine (710 mg, 10.00 mmol, 1.00 equiv) and potassium carbonate (2.76 g, 20.00 mmol, 2.00 equiv) in CH3CN (20 mL) was stirred at 60° C. in an oil bath. After 2 h, the reaction mixture was allowed to reach ambient temperature. The solids were filtered off and the filtrate was concentrated under reduced pressure. The residue was triturated with 1×20 mL of petroleum ether to yield 1.8 g (93%) of the title compound as a yellow solid.

Workup

  1. customto reach ambient temperature
  2. filtrationThe solids were filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was triturated with 1×20 mL of petroleum ether

Sources & evidence

ORD record
ord-0bdde35aaa0c4ac2b570c8202a064e76
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Linked notes

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