Hydrochloric Acid → 2-Methoxy-5-ethyl-6-methylnicotinaldehyde

HRID 2081531Notes

Reaction equation

HRID 2081531 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]#N)=[CH:7][C:6]([CH2:11][CH3:12])=[C:5]([CH3:13])[N:4]=1.[H-].C([Al+]CC(C)C)C(C)C.C1C[O:27]CC1.Cl.C(=O)(O)[O-].[Na+]>O1CCCC1.O>[CH3:1][O:2][C:3]1[N:4]=[C:5]([CH3:13])[C:6]([CH2:11][CH3:12])=[CH:7][C:8]=1[CH:9]=[O:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 104422282-Methoxy-3-cyano-5-ethyl-6-methylpyridineHCID 86597605diisobutylaluminium hydride THF

Product 1

HCID 102616792-Methoxy-5-ethyl-6-methylnicotinaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methoxy-3-cyano-5-ethyl-6-methylpyridine (1.0 g, 5.68 mmol) in dry tetrahydrofuran (50 mL) under a nitrogen atmosphere and cooled to -70° C., was added 1.3M diisobutyl aluminum hydride/THF (17.4 mL, 22.7 mmol). The resulting mixture was allowed to warm to room temperature and stir for 15-20 hours. The reaction mixture was acidified with 1N hydrochloric acid and then neutralized with aqueous sodium bicarbonate. Water was then added and the product extracted into diethyl ether. The etheral extract was dried (Na2SO4), filtered and the solvent evaporated. This residue was flash chromatographed on silica gel eluting with 10% diethyl ether/pentane to give the product.

Workup

  1. extractionthe product extracted into diethyl ether
  2. extractionThe etheral extract
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customchromatographed on silica gel eluting with 10% diethyl ether/pentane
  7. customto give the product

Sources & evidence

ORD record
ord-f3090cafb0db46b293fc28579f192993
Source dataset
uspto-grants-1993_02
Patent number
US05185251

Reaction notes

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