Selenium Dioxide → HCID 14010755, compound

HRID 255673Notes

Reaction equation

HRID 255673 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20]([CH3:21])=[CH:19][C:18](=[O:22])[C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12]2)=[C:7]([CH3:23])[CH:6]=1)(=[O:3])[CH3:2].[Se](=O)=[O:25]>O1CCOCC1>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20]([CH:21]=[O:25])=[CH:19][C:18](=[O:22])[C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12]2)=[C:7]([CH3:23])[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 20183847HCID 20183847, compound

Product 1

HCID 14010755HCID 14010755, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In 315 ml of dioxane was dissolved 10.5 g of methyl 1-(4-acetoxy-2-methylphenyl)-6-methyl-4-oxo-1,4-dihydronicotinate under heating, and 4.43 g of selenium dioxide was added thereto. They were reacted at 100° C. for 2 hours. After cooling the reaction mixture, to room temperature, selenium was removed by filtration, and then the solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform/ethanol (25:1 by volume) mixture) to obtain 7.9 g of methyl 1-(4-acetoxy-2-methylphenyl)-6-formyl-4-oxo-1,4-dihydronicotinate having a melting point of 216°-217° C.

Workup

  1. temperatureunder heating
  2. customThey were reacted at 100° C. for 2 hours
  3. temperatureAfter cooling the reaction mixture
  4. customto room temperature, selenium was removed by filtration
  5. customthe solvent was removed by distillation under reduced pressure
  6. customThe residue was purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform/ethanol (25:1 by volume) mixture)

Sources & evidence

ORD record
ord-015069a57ef44dec9c5f90e1b7788f77
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

Loading…