Hydrochloric Acid → Methyl 8-methylquinoline-5-carboxylate

HRID 11873Notes

Reaction equation

HRID 11873 reaction equation
[CH3:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]([C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.Cl.[CH3:16]O>>[CH3:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]([C:12]([O:14][CH3:16])=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 129507838-Methylquinoline-5-carboxylic acid

Product 1

HCID 12950789Methyl 8-methylquinoline-5-carboxylate

Procedure

The compound obtained in Example 87-2 (1 g) was dissolved in methanol (25 ml). The solution was stirred for 15 hours while blowing hydrochloric acid gas, and the solvent was removed by distillation. The obtained residue was dissolved in water and 1 mol/l sodium hydroxide aqueous solution was added to cause a solid substance to precipitate. The solid was collected by filtration and the filtrate was extracted with chloroform. The extract was dried over anhydrous sodium sulfate and the solvent was removed by distillation to obtain a solid. The solid was combined with the previously collected solid and purified by silica gel column chromatography (20 g, chloroform) to obtain the title compound (0.7337 g) as a white solid.

Workup

  1. customthe solvent was removed by distillation
  2. dissolutionThe obtained residue was dissolved in water
  3. addition1 mol/l sodium hydroxide aqueous solution was added
  4. customto precipitate
  5. filtrationThe solid was collected by filtration
  6. extractionthe filtrate was extracted with chloroform
  7. dry with materialThe extract was dried over anhydrous sodium sulfate
  8. customthe solvent was removed by distillation
  9. customto obtain a solid
  10. custompurified by silica gel column chromatography (20 g, chloroform)

Sources & evidence

ORD record
ord-7caa3397b14e44faa54906917a8e33b6
Source dataset
uspto-grants-2006_08
Patent number
US07098215B2

Reaction notes

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