Hydrochloric Acid → 7-(2,5-Dibromothiophen-3-yl)-5-(1-hydroxyguanidin-3-yl)imino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride

Temperature

90 °C

To a mixture of 7-(2,5-dibromothiophen-3-yl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.07 g) and 1-amino-3-hydroxyguanidine p-toluenesulfonate (58 mg) were added ethanol (1.5 ml) and concentrated hydrochloric acid (0.04 ml), and the mixture was stirred at 90° C. for 2 hours. Under reduced pressure, the solvent was evaporated, and to the residue was added 0.2N sodium hydroxide solution (10 ml). The mixture was extracted with ethyl acetate (30 ml) and tetrahydrofuran (20 ml). The organic layer was washed with water, to which was added concentrated hydrochloric acid (0.02 ml). The mixture was concentrated, and to the residue was added ethanol (1 ml). To the solution was added ether (0.2 ml), and the mixture was stirred for 3 hours. Precipitated crystals were filtered, washed with a mixture of ethanol/ether and dried to give 7-(2,5-dibromothiophen-3-yl)-5-(1-hydroxyguanidin-3-yl)imino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 126) (0.27 g) as pale yellow crystals.

1. customUnder reduced pressure, the solvent was evaporated
2. additionto the residue was added 0.2N sodium hydroxide solution (10 ml)
3. extractionThe mixture was extracted with ethyl acetate (30 ml) and tetrahydrofuran (20 ml)
4. washThe organic layer was washed with water, to which
5. additionwas added concentrated hydrochloric acid (0.02 ml)
6. concentrationThe mixture was concentrated
7. additionto the residue was added ethanol (1 ml)
8. additionTo the solution was added ether (0.2 ml)
9. stirringthe mixture was stirred for 3 hours
10. customPrecipitated crystals
11. filtrationwere filtered
12. washwashed with a mixture of ethanol/ether
13. customdried

ORD record

ord-5531f1942e174c7ea840f8852df2c5dd

Source dataset

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06350749B1