Hydrochloric Acid → 4-Methylpyridine-2-carbaldehyde

HRID 742469Notes

Reaction equation

HRID 742469 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][N+:4]=1[O-])#N.Cl.O.C(=O)(O)[O-:14].[Na+]>C(Cl)Cl>[CH3:9][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([CH:1]=[O:14])[CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 37251652-Cyano-4-methylpyridin-1-ium-1-olate

Product 1

HCID 100118944-Methylpyridine-2-carbaldehydeYield 14.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-cyano-4-methylpyridine-N-oxide (3.29 g, 0.0279 mol) in 164 mL of methylene chloride at -78° C. was added 27.6 mL of DIBAL(H) and the mixture was stirred at -78 ° C. for 2 h. To the above mixture was added 13 mL of HCl (conc.) and 52 mL of water, and the mixture was warmed to room temperature. To the aqueous layer was added sodium bicarbonate solution, the solution was extracted with ether, and the combined organic layer was concentrated in vacuo. The residue was purified by chromatography on silica (ether) to afford 0.5 g (14.8%) of 4-methylpyridine-2-carboxaldehyde, as an oil.

Workup

  1. temperaturethe mixture was warmed to room temperature
  2. extractionthe solution was extracted with ether
  3. concentrationthe combined organic layer was concentrated in vacuo
  4. customThe residue was purified by chromatography on silica (ether)

Sources & evidence

ORD record
ord-fd273ddc774046a78311e8788a0eaf7b
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

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