Hydrogen Peroxide → 3-Chloro-6,7-dihydro-5h-cyclopenta[b]pyridine 1-oxide

Temperature

70 °C

A solution of 3-chloro-6,7-dihydro-5H-[1]pyrindine (3.03 g, 19.7 mmol) in acetic acid (19.7 ml) was treated at room temperature with hydrogen peroxide (3.45 ml, 39.5 mmol). The mixture was heated to 70° C. and stirred at this temperature overnight. After completion, the reaction mixture was allowed to cool and was concentrated at reduced pressure. Water was added and the mixture was evaporated again. This procedure was repeated another 2 times. The residue was dissolved in ethyl acetate, washed with a saturated aqueous solution of sodium hydrogen carbonate and brine, then dried over sodium sulphate and evaporated at reduced pressure. The crude 3-chloro-6,7-dihydro-5H-[1]pyrindine 1-oxide was obtained as dark green crystals (2.07 g, 62%). (calculated) C8H8ClNO [169.61]; (found) [M+H]+=170.

1. temperatureto cool
2. concentrationwas concentrated at reduced pressure
3. additionWater was added
4. customthe mixture was evaporated again
5. dissolutionThe residue was dissolved in ethyl acetate
6. washwashed with a saturated aqueous solution of sodium hydrogen carbonate and brine
7. dry with materialdried over sodium sulphate
8. customevaporated at reduced pressure

ORD record

ord-e49ee86c8e324c05a138f0f4379ee78f

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242943B2