Hydrochloric Acid → HCID 178425376, compound

To a solution of 7-(5-chloro-2-methylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (1.0 g) and aminoguanidine hydrochloride (0.46 g) in ethanol (30 ml) were added concentrated hydrochloric acid (0.9 ml) and water (0.9 ml), and the mixture was refluxed for 5 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in water. The mixture was washed with ethyl acetate, and to the aqueous layer was added sodium hydrogen carbonate solution to make it alkaline. The solution was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solution was concentrated, and the residue was dissolved in ethanol. To the solution was added 1N hydrochloric acid (10 ml), and the mixture was concentrated. Precipitated crystals were recrystallized from ethanol to give 7-(5-chloro-2-methylphenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 164) (1.4 g) as colorless crystals.

1. temperaturethe mixture was refluxed for 5 hours
2. customUnder reduced pressure, the solvent was evaporated
3. dissolutionthe residue was dissolved in water
4. washThe mixture was washed with ethyl acetate
5. additionto the aqueous layer was added sodium hydrogen carbonate solution
6. extractionThe solution was extracted with ethyl acetate
7. washthe organic layer was washed with water and saturated brine
8. dry with materialdried with magnesium sulfate
9. concentrationUnder reduced pressure, the solution was concentrated
10. dissolutionthe residue was dissolved in ethanol
11. additionTo the solution was added 1N hydrochloric acid (10 ml)
12. concentrationthe mixture was concentrated
13. customPrecipitated crystals
14. customwere recrystallized from ethanol

ORD record

ord-27f00aea022b44a58f65ea015445abd1

Source dataset

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06350749B1