Ethyl Acetate → 5-Nitro-2-(1-pyrrolidinyl)pyridine

HRID 413268

Reaction equation

HRID 413268 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.CCOC(C)=O>CN(C=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 3168235-Nitro-2-(1-pyrrolidinyl)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring mixture of 2-chloro-5-nitropyridine (5.0 g, 31.5 mmol), potassium carbonate (7.0 g, 50.4 mmol), in 65 ml of DMF add pyrrolidine (6.7 g, 95 mmol) and stir at room temperature for 72 h. Dilute reaction mixture with 100 ml EtOAc and wash 2 times with 100 ml saturated NaHCO3, and 2 times with 100 ml of brine. Dry organics over Na2SO4, and evaporate in vacuo to obtain 5-nitro-2-pyrrolidin-1-yl-pyridine. Mass spec.: m+1=194 (AP+).

Workup

  1. additionDilute
  2. washwash 2 times with 100 ml saturated NaHCO3, and 2 times with 100 ml of brine
  3. customDry organics over Na2SO4, and evaporate in vacuo

Sources & evidence

ORD record
ord-849e704475b84796bac2f6bf0cb50237
Source dataset
uspto-grants-2003_05
Patent number
US06566367B2

Linked notes

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