Pyridine → HCID 86750207, compound

Temperature

90 °C

Titanium tetrachloride (2.58 ml, 23.4 mmol) was added dropwise to a solution of pyridine (7.60 ml, 93.6 mmol) in 1,2-dichloroethane (40 ml) and, after completion of the addition, the reaction mixture was heated under reflux for 30 minutes in an argon atmosphere. After cooling of the reaction mixture, a solution of 3,5,6-trimethyl-2-(2-methyl-2-propenyl)-1,4-benzoquinone (2.40 g, 11.7 mmol) and aniline (3.35 ml, 35.1 mmol) in 1,2-dichloroethane (5 ml) was added thereto and the mixture was stirred at 90° C. for 2 hours in an argon atmosphere. The reaction mixture was cooled and filtered through Cerite and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate, 98:2). The resulting compound was dissolved in tetrahydrofuran (10 ml) and to the solution was added a solution of sodium hydrosulfite (12 g, 69 mmol) in water (30 ml). The mixture was stirred at room temperature for 30 minutes. The organic phase was separated and the aqueous phase was extracted with ethyl acetate. The extract was combined with the organic phase and the mixture was washed with water and dried and the solvent was distilled oil under reduced pressure. The residue was purified by silica gel chromatography (hexaneethyl acetate, 95:5) to obtain the desired compound as oil (1.41 g, yield: 42.8%).

1. additionafter completion of the addition
2. temperaturethe reaction mixture was heated
3. temperatureunder reflux for 30 minutes in an argon atmosphere
4. temperatureAfter cooling of the reaction mixture
5. temperatureThe reaction mixture was cooled
6. filtrationfiltered through Cerite
7. concentrationthe filtrate was concentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate, 98:2)
9. dissolutionThe resulting compound was dissolved in tetrahydrofuran (10 ml) and to the solution
10. stirringThe mixture was stirred at room temperature for 30 minutes
11. customThe organic phase was separated
12. extractionthe aqueous phase was extracted with ethyl acetate
13. washthe mixture was washed with water
14. customdried
15. distillationthe solvent was distilled oil under reduced pressure
16. customThe residue was purified by silica gel chromatography (hexaneethyl acetate, 95:5)

ORD record

ord-b909a33f92dd493cbef68fb19841efdf

Source dataset

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05594154