2-Nitropropane → HCID 86686339, compound

HRID 1043906Notes

Reaction equation

HRID 1043906 reaction equation
C[O-].[Na+].[N+](C(C)C)([O-])=[O:5].[Br:10][C:11]1[C:12]([CH2:19]Br)=[N:13][C:14]([CH3:18])=[CH:15][C:16]=1[CH3:17]>CO>[Br:10][C:11]1[C:12]([CH:19]=[O:5])=[N:13][C:14]([CH3:18])=[CH:15][C:16]=1[CH3:17]

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 10942334Sodium MethoxideHCID 86686337HCID 86686337, compound

Product 1

HCID 86686339HCID 86686339, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (581 mg) was added to a solution of 2-nitropropane (0.982 mL) in methanol (20 mL) at room temperature, and the mixture was stirred at the same temperature for 20 minutes. 3-bromo-2-(bromomethyl)-4,6-dimethylpyridine obtained in Preparation Example 33(1) (1.00 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 (467 mg).

Workup

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

Sources & evidence

ORD record
ord-929c0fab8bfb4ccca69569d10e4728d0
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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