Hydrochloric Acid → HCID 18979213, compound

In THF (8.5 ml)-DMF (0.1 ml) was dissolved 6-cyano-6-(1-naphthyl)hexanoic acid (4.0 g) (15 mmol) followed by dropwise addition of oxalyl chloride (3.2 ml) (37.5 mmol) at room temperature. After 15 minutes of stirring, the excess oxalyl chloride was distilled off under reduced pressure. The residue was dissolved in dichloromethane (63 ml) and the solution was added to a solution (63 ml) of hydroxylamine hydrochloride (3.13 g) (45 mmol) in saturated aqueous sodium hydrogen carbonate solution with ice-cooling. The reaction was carried out at room temperature for 2 hours, at the end of which time the reaction mixture was made weakly acidic with concentrated hydrochloric acid. The organic layer was washed with saturated aqueous sodium chloride solution (50 ml), dried over anhydrous sodium sulfate, and purified by silica gel column chromatography (hexane-ethyl acetate=1:9) to provide the title compound (4.08 g) (yield 96.3%) as colorless oil.

1. distillationthe excess oxalyl chloride was distilled off under reduced pressure
2. dissolutionThe residue was dissolved in dichloromethane (63 ml)
3. temperaturecooling
4. waitThe reaction was carried out at room temperature for 2 hours, at the end of which time
5. washThe organic layer was washed with saturated aqueous sodium chloride solution (50 ml)
6. dry with materialdried over anhydrous sodium sulfate
7. custompurified by silica gel column chromatography (hexane-ethyl acetate=1:9)

ORD record

ord-8e1045f280de41be9186faec484e327a

Source dataset

uspto-grants-1998_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05804601