Hydrochloric Acid → HCID 22266502, compound

1-Butyl-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carboaldehyde (1-015-04) (160 mg, 0.69 mmol) was dissolved in methylene chloride (10 mL), and to the reaction mixture were added NaH2PO4·H2O (190 mg, 1.38 mmol) and meta-chloroperbenzoic acid (237 mg, 1.38 mmol). The reaction mixture was stirred at room temperature for 30 min, and to the reaction mixture was added 5% aqueous sodium thiosulfate solution (20 mL). The reaction mixture was extracted with ethyl acetate (50 mL), washed with aqueous saturated sodium hydrogen carbonate solution (20 mL) and brine (20 mL), dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue was dissolved in ethanol (5 mL), 2 mol/L aqueous sodium hydroxide solution (0.35 mL, 0.7 mmol) was added to the reaction mixture, and the reaction mixture was stirred at room temperature for 30 min. To the reaction mixture was added 0.2 mol/L diluted hydrochloric acid (7 mL), and the reaction mixture was extracted with ethyl acetate (25 ml), washed brine (10 mL), dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (toluene/ethyl acetate) to give 1-butyl-3-hydroxy-5,6,7,8-tetrahydro-1H-quinoline-2-one (1-015-05) (82 mg, 54%) as a pale brown color crystal.

1. extractionThe reaction mixture was extracted with ethyl acetate (50 mL)
2. washwashed with aqueous saturated sodium hydrogen carbonate solution (20 mL) and brine (20 mL)
3. dry with materialdried over anhydrous magnesium sulfate
4. customevaporated under reduced pressure
5. dissolutionThe residue was dissolved in ethanol (5 mL)
6. stirringthe reaction mixture was stirred at room temperature for 30 min
7. extractionthe reaction mixture was extracted with ethyl acetate (25 ml)
8. washwashed brine (10 mL)
9. dry with materialdried over anhydrous magnesium sulfate
10. customevaporated under reduced pressure
11. customThe obtained residue was purified by silica gel column chromatography (toluene/ethyl acetate)

ORD record

ord-e4fd37b9b5ec4615b0d0fae229647578

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08088924B2