Pyridine → 7-chloro-3,4-dihydro-2H-naphthalen-1-one-O-methyl-oxime

Temperature

24 °C

To a stirred solution of 7-chloro-1-tetralone CAS: 26673-32-5 (5.0 g; 27.68 mmol) in methanol (55 ml) was added pyridine (2.87 ml; 34.05 mmol) followed by a portion wise addition of methoxyamine hydrochloride (2.84 g; 34.05 mmol). The reaction mixture was stirred at 24° C. for 16 h under nitrogen. Methanol was removed under reduced pressure, the residue poured in water (300 ml) and 1N hydrochloric acid was added (100 ml). The solution was extracted with dichloromethane (3×150 ml). Combined organic layers were washed with water (300 ml) and dried over sodium sulfate. The solvent was removed in vacuo to afford 6.22 g (100% of theory) of crude 7-chloro-3,4-dihydro-2H-naphthalen-1-one-O-methyl-oxime as a brown oil.

1. customMethanol was removed under reduced pressure
2. additionthe residue poured in water (300 ml)
3. addition1N hydrochloric acid was added (100 ml)
4. extractionThe solution was extracted with dichloromethane (3×150 ml)
5. washCombined organic layers were washed with water (300 ml)
6. dry with materialdried over sodium sulfate
7. customThe solvent was removed in vacuo

ORD record

ord-d23521188cca4cfaab81244a486e6095

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653003B2