1,2-Cyclohexanedione → HCID 178439981, compound

Temperature

-30 °C

1,2-cyclohexanedione (5.4 g, 48 mM) was added all at once to a methanol solution (80 ml) of norvalineamide hydrochloride (6.1 g, 40 mM) at -30° C., and aqueous 12.5N NaOH (8 ml) was added dropwise thereto. The reaction mixture was stirred at -30° C. for 30 mins., cooling was removed, and the mixture stirred at room temperature for 3 hours. Conc. hydrochloric acid (10 ml) was added to the reaction mixture under ice-cooling, sodium bicarbonate (8 g) was added after 10 mins., the methanol then being distilled off in vacuo. The residue was extracted with chloroform, and the extract washed with water, dried with anhydrous sodium sulfate and concentrated in vacuo. The residue was washed with acetone and recrystallized from acetone to obtain the product as colorless crystals (3.8 g., yield: 50%, m.p.: 131°-133° C.

1. temperature, cooling
2. customwas removed
3. stirringthe mixture stirred at room temperature for 3 hours
4. additionConc. hydrochloric acid (10 ml) was added to the reaction mixture under ice-
5. temperaturecooling
6. additionsodium bicarbonate (8 g) was added after 10 mins
7. distillation, the methanol then being distilled off in vacuo
8. extractionThe residue was extracted with chloroform
9. washthe extract washed with water
10. dry with materialdried with anhydrous sodium sulfate
11. concentrationconcentrated in vacuo
12. washThe residue was washed with acetone
13. customrecrystallized from acetone

ORD record

ord-bc94c18fc10549209fcb7718d1720408

Source dataset

uspto-grants-1989_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04877877