2,4,6-Trimethylpyridine → HCID 86639587, compound

HRID 1910774Notes

Reaction equation

HRID 1910774 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.C([O-])(=O)C.[Na+].[N+:15]([C:18]1[CH:27]=[CH:26][C:21](/[CH:22]=[CH:23]/[CH:24]=O)=[CH:20][CH:19]=1)([O-:17])=[O:16]>C(OC(=O)C)(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH:9]=[CH:24][CH:23]=[CH:22][C:21]2[CH:26]=[CH:27][C:18]([N+:15]([O-:17])=[O:16])=[CH:19][CH:20]=2)[N:3]=1

Participants

5

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 517045Sodium AcetateHCID 53541354-Nitrocinnamaldehyde

Product 1

HCID 86639587HCID 86639587, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

2,4,6-Trimethylpyridine (2.24 mL, 16.9 mmol) and sodium acetate (0.92 g, 11.3 mmol) were added to a solution of trans-4-nitrocinnamaldehyde (1.0 g, 5.64 mmol) in acetic anhydride (20 mL). The reaction mixture was refluxed for 8 h, then brought to room temperature and quenched with 5% sodium bicarbonate solution (40 mL). The compound was extracted with ethyl acetate and the organic layer was washed with water, brine solution, dried over anhydrous sodium sulfate, filtered and concentrated. The crude compound was purified by column chromatography over silica gel (60-120 mesh) using 30% ethyl acetate in hexane as eluent to afford 2,4-dimethyl-6-[4-(4-nitro-phenyl)-buta-1,3-dienyl]-pyridine (800 mg, 51%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 8 h
  2. custombrought to room temperature
  3. customquenched with 5% sodium bicarbonate solution (40 mL)
  4. extractionThe compound was extracted with ethyl acetate
  5. washthe organic layer was washed with water, brine solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude compound was purified by column chromatography over silica gel (60-120 mesh)

Sources & evidence

ORD record
ord-a0bfb46cecaa44a789206d8bf47e1d5b
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

Loading…