Nitromethane → HCID 118343008, compound

HRID 2202660Notes

Reaction equation

HRID 2202660 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:10])[C:7]=1[CH:8]=[O:9].[N+:11]([CH3:14])([O-:13])=[O:12].C[O-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:10])[C:7]=1[CH:8]([OH:9])[CH2:14][N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 27629883,5-Dichloro-4-pyridinecarboxaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 118343008HCID 118343008, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,5-dichloro-4-pyridinecarboxaldehyde (2.3 g, 13.3 mmol) in MeOH (25 mL) were added nitromethane (2.2 mL, 39.9 mmol) and sodium methoxide (861 mg, 15.9 mmol). After addition, the mixture was stirred for 1 h. The reaction mixture was quenched by adding 2 M aqueous HCl (7 mL) and extracted with EtOAc. The organic layer washed with brine×2 and dried over MgSO4. After the solvent was removed, the residue was purified by column chromatography on silica gel to give compound A1-1 (2.8 g, 90%) as a white solid.

Workup

  1. additionAfter addition
  2. customThe reaction mixture was quenched
  3. additionby adding 2 M aqueous HCl (7 mL)
  4. extractionextracted with EtOAc
  5. washThe organic layer washed with brine×2
  6. dry with materialdried over MgSO4
  7. customAfter the solvent was removed
  8. customthe residue was purified by column chromatography on silica gel
  9. customto give compound A1-1 (2.8 g, 90%) as a white solid

Sources & evidence

ORD record
ord-0ba4b6bd53f44d86818ec9c638c66559
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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