Pyrrolidine → 3-Azulen-1-ylmethylene-1-benzyl-1,3-dihydro-indol-2-one

1-Formylazulene (1 mmol) was dissolved in 20 mL ethanol. 223 mg 1-benzylindolin-2-one (1 mmol) and 20 mL ethanol were then added. Next, a 2 mL solution (1 mmol) containing 1M pyrrolidine and ethanol was added to react at room temperature for three days. After removal of solvent, the resulting solution was extracted by 150 mL ethyl acetate and 50 mL water. The resulting solution was extracted again by 50 mL citric acid aqueous solution and ethyl acetate. The ethyl acetate layer was collected, dried with anhydrous magnesium sulfate, filtered, and concentrated under vacuum. Next, methanol was added and ultrasonically shaken at 40° C. for 1 hour. After filtration, washing by methanol, and drying, Compound 002 (315 mg, 87%) was obtained.

1. additionwas added
2. customto react at room temperature for three days
3. customAfter removal of solvent
4. extractionthe resulting solution was extracted by 150 mL ethyl acetate and 50 mL water
5. extractionThe resulting solution was extracted again by 50 mL citric acid aqueous solution and ethyl acetate
6. customThe ethyl acetate layer was collected
7. dry with materialdried with anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated under vacuum
10. additionNext, methanol was added
11. filtrationAfter filtration
12. washwashing by methanol
13. customdrying

ORD record

ord-e4cbc6c77b6247c0b34c10def7e47f39

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07714146B2