Trifluoroacetic acid → HCID 45357692, compound

To a solution of 3.5 g of the compound of step (a) in 15 ml of methylene chloride was added trifluoroacetic acid (39 ml) and the mixture was stirred at ambient temperature for three hours. The mixture was then concentrated in vacuo. The residue was dissolved in methanol (30 ml) and 18M H2SO4 (3 ml) was added and the mixture was stirred overnight. The mixture was then poured into a solution of sodium carbonate in water, extracted three times with chloroform, dried over MgSO4, filtered and concentrated in vacuo to give a yellow solid. The solid was dissolved in methanol (10 ml) and hydrazine (2 ml) was added to this solution and the mixture was heated to reflux for one hour. The mixture was then concentrated in vacuo. The resulting solid was suspended in toluene (50 ml) and heated to reflux in an apparatus equipped with a Dean-Stark trap for two hours. The reaction mixture was then allowed to cool, and the product was filtered off to give 1.82 g of the subtitle compound as a tan solid.

1. concentrationThe mixture was then concentrated in vacuo
2. dissolutionThe residue was dissolved in methanol (30 ml)
3. addition18M H2SO4 (3 ml) was added
4. stirringthe mixture was stirred overnight
5. additionThe mixture was then poured into a solution of sodium carbonate in water
6. extractionextracted three times with chloroform
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto give a yellow solid
11. temperaturethe mixture was heated
12. temperatureto reflux for one hour
13. concentrationThe mixture was then concentrated in vacuo
14. temperatureheated
15. temperatureto reflux in an apparatus
16. customequipped with a Dean-Stark trap for two hours
17. temperatureto cool
18. filtrationthe product was filtered off

ORD record

ord-f2db99493007424083102b79b98e7329

Source dataset

uspto-grants-1999_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05902814