3-[2-(benzoxazol-2-yl)ethenyl]-5-ethyl-6-methyl-2-(1H)-pyridinone → L 696229

HRID 273683Notes

Reaction equation

HRID 273683 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]=[CH:11][C:12]1[C:13](=[O:21])[NH:14][C:15]([CH3:20])=[C:16]([CH2:18][CH3:19])[CH:17]=1>CO.C(O)C.C1COCC1.[Pd]>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][CH2:11][C:12]1[C:13](=[O:21])[NH:14][C:15]([CH3:20])=[C:16]([CH2:18][CH3:19])[CH:17]=1

Participants

4

Reactant 1

HCID 4548263-[2-(benzoxazol-2-yl)ethenyl]-5-ethyl-6-methyl-2-(1H)-pyridinone

Product 1

HCID 72352L 696229

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 66624091Ethanol tetrahydrofuran methanolSolvent

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-91cb3608adcf4d889c0a35cce978bfee
Source dataset
uspto-grants-1995_02
Patent number
US05387512

Reaction notes

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