Hydrochloric Acid → HCID 22266526, compound

Temperature

-78 °C

DMSO (0.54 mL, 7.64 mmol) was dissolved in methylene chloride (27 mL) and the solvent was cooled at −78° C. To the solvent were added dropwise oxalyl chloride (0.4 mL, 4.58 mL), a solution of 1-butyl-3-hydroxymethyl-5,6,7,8-tetrahydro-1H-quinoline-2-one (1-015-03) (0.9 g, 3.82 mmol) in methylene chloride (20 mL) and triethylamine (1.33 mL, 9.55 mmol), and then the reaction mixture was stirred at −78° C. for 5 min. The reaction mixture was gradually warmed to room temperature, and stirred at room temperature for 20 min. To the reaction mixture was added 1 mol/L diluted hydrochloric acid (50 mL), and the reaction mixture was extracted with ethyl acetate (200 mL), washed with aqueous saturated sodium hydrogen carbonate solution (50 mL) and brine (50 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-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carboaldehyde (1-015-04) (0.5 g, 56%) as a pale yellow bubbly substance.

1. temperatureThe reaction mixture was gradually warmed to room temperature
2. extractionthe reaction mixture was extracted with ethyl acetate (200 mL)
3. washwashed with aqueous saturated sodium hydrogen carbonate solution (50 mL) and brine (50 mL)
4. dry with materialdried over anhydrous magnesium sulfate
5. customevaporated under reduced pressure
6. customThe obtained residue was purified by silica gel column chromatography (toluene/ethyl acetate)

ORD record

ord-799d3ab7cb9a48098de82077d09235e7

Source dataset

uspto-grants-2005_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06977266B2