Phenanthridine → HCID 22482336, compound

A stirred solution of phenanthridine (3.58 g, 20 mmol) in anhydrous diethyl ether (20 mL) was cooled to −30° C., and treated drop-wise under nitrogen via syringe with a solution of 1.4 M methyllithium in diethyl ether (14.5 mL, 20.3 mmol). The yellow solution was warmed to room temperature and stirred for 15 minutes. The mixture was cooled to −78° C., and treated with 3,4-dimethoxybenzenesulfonyl chloride (4.73 g, 20 mmol) as a solid in a single aliquot. The reaction mixture was warmed slowly to room temperature over one hour, poured into a 1 N aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic phase was washed sequentially with water, 1 N hydrochloric acid, and a saturated, aqueous, sodium chloride solution. After drying over anhydrous sodium sulfate, the organic phase was filtered through a short column of silica gel, and the filtrate evaporated in vacuo to yield a crude yellow solid (5.3 g, 67%). Crystallization of the solid from a mixture of diethyl ether-hexane yielded the title compound (2.93 g) and a second crop (0.8 g) (Total: 3.73 g, 9.43 mmol, 47%) as a homogeneous, off-white, crystalline solid, m.p. 131-133° C.;

1. temperatureThe mixture was cooled to −78° C.
2. temperatureThe reaction mixture was warmed slowly to room temperature over one hour
3. extractionextracted with ethyl acetate
4. washThe organic phase was washed sequentially with water, 1 N hydrochloric acid
5. dry with materialAfter drying over anhydrous sodium sulfate
6. filtrationthe organic phase was filtered through a short column of silica gel
7. customthe filtrate evaporated in vacuo
8. customto yield a crude yellow solid (5.3 g, 67%)
9. customCrystallization of the solid
10. additionfrom a mixture of diethyl ether-hexane

ORD record

ord-f6c5f15c641b47229477c3f7a55bfa74

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06894061B2