Hydrochloric Acid → HCID 22449518, compound

The compound obtained in (4) above (42 gm) was dissolved into 100 ml of methanol. After the addition of 200 ml of 1 N hydrochloric acid, the mixture was stirred for 3 hours at room temperature. The reaction mixture was concentrated to 200 ml and, after acidifying with the addition of concentrated hydrochloric acid, extracted three times with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated, and to the residue were added 100 ml of dichloromethane, then 17 gm of sodium carbonate and 12 ml of thionyl chloride. The mixture was heated under reflux for 2 hours, and then cooled to room temperature to remove insoluble substances by filtration. The filtrate was concentrated and 200 ml of 1,2-dichloromethane and 40 gm of aluminum chloride were added to the residue. The mixture was stirred for 3 hours at 70° C., then for 1 hour at 90° C. The reaction product was poured into ice-cooled water and extracted with chloroform. The extract was washed with water, saturated sodium bicarbonate, and saturated brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was subjected to silica gel column chromatography using chloroform-ethyl acetate (7:3) as an eluant to obtain fractions containing the target compound. The fractions were concentrated to obtain 17 gm of the title compound.

1. concentrationThe reaction mixture was concentrated to 200 ml
2. additionafter acidifying with the addition of concentrated hydrochloric acid
3. extractionextracted three times with ethyl acetate
4. washThe ethyl acetate layer was washed with water and saturated brine in this order
5. dry with materialdried over anhydrous sodium sulfate
6. customThe solvent was evaporated
7. additionto the residue were added 100 ml of dichloromethane
8. temperatureThe mixture was heated
9. temperatureunder reflux for 2 hours
10. temperaturecooled to room temperature
11. customto remove insoluble substances
12. filtrationby filtration
13. concentrationThe filtrate was concentrated
14. addition200 ml of 1,2-dichloromethane and 40 gm of aluminum chloride were added to the residue
15. stirringThe mixture was stirred for 3 hours at 70° C.
16. waitfor 1 hour at 90° C
17. additionThe reaction product was poured into ice-
18. temperaturecooled water
19. extractionextracted with chloroform
20. washThe extract was washed with water, saturated sodium bicarbonate, and saturated brine in this order
21. dry with materialdried over anhydrous sodium sulfate
22. customThe solvent was evaporated
23. customto obtain fractions
24. additioncontaining the target compound
25. concentrationThe fractions were concentrated

ORD record

ord-0e3ccc0cf372429ea65946057c65ddad

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06407115B1