Pyridinium chloride → 3-(2-(4,7-Dimethylbenzoxazol-2-yl)ethyl)-5-ethyl-6-methylpyridin-2(1H)-one

HRID 1032998Notes

Reaction equation

HRID 1032998 reaction equation
C[O:2][C:3]1[C:8]([CH2:9][CH2:10][C:11]2[O:12][C:13]3[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]([CH3:21])[C:14]=3[N:15]=2)=[CH:7][C:6]([CH2:22][CH3:23])=[C:5]([CH3:24])[N:4]=1.Cl.N1C=CC=CC=1>O>[CH3:21][C:16]1[C:14]2[N:15]=[C:11]([CH2:10][CH2:9][C:8]3[C:3](=[O:2])[NH:4][C:5]([CH3:24])=[C:6]([CH2:22][CH3:23])[CH:7]=3)[O:12][C:13]=2[C:19]([CH3:20])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 10381616HCID 10381616, compound

Product 1

HCID 4534443-(2-(4,7-Dimethylbenzoxazol-2-yl)ethyl)-5-ethyl-6-methylpyridin-2(1H)-oneYield 42.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of crude 2-methoxy-3-[2-(4,7-dimethylbenzoxazol-2-yl)ethyl]-5-ethyl-6-methylpyridine (161 mg, 0.49 mmol) and pyridine hydrochloride (574 mg, 4.97 mmol) was warmed in a pre-heated oil bath at 140° C. for 15 minutes. The cooled residue was diluted with water and the product extracted into chloroform. This extract was dried (Na2SO4), filtered and the solvent evaporated. This residue was chromatographed on silica gel and eluted with a 0.5 to 2.5% methanol/chloroform gradient to yield 65 mg of pure product. The product was crystallized from diethyl ether to give 38 mg, m.p. 151.5°-153° C.

Workup

  1. extractionthe product extracted into chloroform
  2. dry with materialThis extract was dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent evaporated
  5. customThis residue was chromatographed on silica gel
  6. washeluted with a 0.5 to 2.5% methanol/chloroform gradient

Sources & evidence

ORD record
ord-d3b4f28e98b24e458e904a8098a43d5f
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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