Potassium Iodide → HCID 23326429, compound

HRID 1380312Notes

Reaction equation

HRID 1380312 reaction equation
C(CS[C:6]1[N:7]=[N:8][C:9]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]([CH3:23])[C:18](=[O:24])[CH2:17][CH2:16]3)=[C:10]([CH3:12])[N:11]=1)(O)=O.[OH-:25].[K+].[I-].[K+].[CH2:29](Cl)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CO>[CH3:23][N:19]1[C:20]2[C:15](=[CH:14][C:13]([C:9]3[C:10]([CH3:12])=[N:11][C:6](=[O:25])[N:7]([CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:8]=3)=[CH:22][CH:21]=2)[CH2:16][CH2:17][C:18]1=[O:24]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7503Benzyl ChlorideHCID 14797Potassium HydroxideHCID 20232098HCID 20232098, compound

Product 1

HCID 23326429HCID 23326429, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 3-carboxymethylthio-5-methyl-6-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-1,2,4-triazine (7.25 g) in a mixture of 10% aqueous solution of potassium hydroxide (47 ml) and methanol (47 ml) was heated at 60° for 4 hours with stirring. To the mixture were added potassium iodide (0.5 g), benzyl chloride (5.33 g), and methanol (150 ml), refluxed for 8 hours with stirring, and evaporated in vacuo. To the residue was added water and extracted with ethyl acetate. The extract was dried over magnesium sulfate and evaporated in vacuo. The oily residue was purified by column chromatography on silica gel (300 g) with ethyl acetate as an eluent to give 6-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2-benzyl-5-methyl-1,2,4-triazin-3(2H)-one (4.47 g).

Workup

  1. temperaturewas heated at 60° for 4 hours
  2. temperaturerefluxed for 8 hours
  3. stirringwith stirring
  4. customevaporated in vacuo
  5. additionTo the residue was added water
  6. extractionextracted with ethyl acetate
  7. dry with materialThe extract was dried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe oily residue was purified by column chromatography on silica gel (300 g) with ethyl acetate as an eluent

Sources & evidence

ORD record
ord-eeea2965d88f43c58be4f787d08a148c
Source dataset
uspto-grants-1986_04
Patent number
US04581356

Reaction notes

Loading…