3-[2-(benzoxazol-2-yl)ethenyl]-5-ethyl-6-methyl-2-(1H)-pyridinone → 2-Methoxy-5-ethyl-6-methylnicotinaldehyde

HRID 273686Notes

Reaction equation

HRID 273686 reaction equation
O1[C:5]2[CH:6]=[CH:7]C=[CH:9][C:4]=2[N:3]=C1C=CC1C(=O)NC(C)=C(CC)C=1.CO.[CH2:24]([OH:26])C.[CH2:27]1[CH2:31][O:30][CH2:29][CH2:28]1>[Pd]>[CH3:29][O:30][C:31]1[N:3]=[C:4]([CH3:9])[C:5]([CH2:6][CH3:7])=[CH:28][C:27]=1[CH:24]=[O:26]

Participants

4

Reactant 2

HCID 4548263-[2-(benzoxazol-2-yl)ethenyl]-5-ethyl-6-methyl-2-(1H)-pyridinoneHCID 66624091Ethanol tetrahydrofuran methanol

Product 1

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

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 80% pure 3-[2-(benzoxazol-2-yl)ethenyl]-5-ethyl-6-methyl-2-(1H)-pyridinone (200 mg) in methanol/ethanol/THF (25 mL, 1:1:1) was hydrogenated at atmospheric pressure over 5% palladium/charcoal for four hours. After filtering off the catalyst, the solvents were evaporated and the residue flash chromatographed over silica gel. Elution with 2% methanol-98% chloroform gave 75 mg of analytically pure product, mp 155°-156.5° C.

Workup

  1. filtrationAfter filtering off the catalyst
  2. customthe solvents were evaporated
  3. customthe residue flash chromatographed over silica gel
  4. washElution with 2% methanol-98% chloroform
  5. customgave 75 mg of analytically pure product, mp 155°-156.5° C.

Sources & evidence

ORD record
ord-f3f571178e3943a78a64a0d0a61bae24
Source dataset
uspto-grants-1995_02
Patent number
US05387512

Reaction notes

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