2-Nitropropane → HCID 86686335, compound

HRID 1043902Notes

Reaction equation

HRID 1043902 reaction equation
C[O-].[Na+].[N+](C(C)C)([O-])=[O:5].[Br:10][C:11]1[C:12]([CH3:20])=[N:13][C:14]([CH2:18]Br)=[CH:15][C:16]=1[CH3:17]>CO>[Br:10][C:11]1[C:16]([CH3:17])=[CH:15][C:14]([CH:18]=[O:5])=[N:13][C:12]=1[CH3:20]

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 10942334Sodium MethoxideHCID 86686334HCID 86686334, compound

Product 1

HCID 86686335HCID 86686335, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (1.16 g) was added to a solution of 2-nitropropane (1.96 mL) in methanol (40 mL) at mom temperature, and the mixture was stirred at the same temperature for 20 minutes. 3-bromo-6-(bromomethyl)-2,4-dimethylpyridine (2.00 g) was added to the reaction mixture, and the mixture was stirred at 50° C. for five hours. The reaction mixture was concentrated under reduced pressure, and water was added to the residue, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 50%) to give the title compound (565 mg).

Workup

  1. stirringthe mixture was stirred at 50° C. for five hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  3. additionwas added to the residue
  4. extractionfollowed by extraction with ethyl acetate
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 50%)

Sources & evidence

ORD record
ord-d10ae61ca024407689311ea5d8f51888
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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