Ammonia → 3-Chloro-6-methylphenanthridine

온도

120 °C

N-(4-Chloro-1,1′-biphenyl-2-yl)acetamide (2.65 g, 10.8 mmol) was mixed with polyphosphoric acid (50 g) and heated to 120° C. with vigorous stirring for 12 hours. The hot reaction mixture was poured into a beaker containing ice and stirred vigorously until homogeneous. The solution was neutralized to a pH>8 with concentrated aqueous ammonia. A white precipitate formed and was filtered. The white solid was dissolved in ethyl acetate (250 mL) and re-filtered. The filtrate was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and the solvent concentrated in vacuo to a brown solid. The brown solid was purified by trituration with ethyl acetate/hexane to afford the title compound as white crystals (2.28 g, 93%), m.p. 129-131° C.;

1. additionThe hot reaction mixture was poured into a beaker
2. additioncontaining ice
3. stirringstirred vigorously until homogeneous
4. customA white precipitate formed
5. filtrationwas filtered
6. dissolutionThe white solid was dissolved in ethyl acetate (250 mL)
7. filtrationre-filtered
8. washThe filtrate was washed with a saturated aqueous sodium chloride solution
9. dry with materialdried over anhydrous sodium sulfate
10. filtrationfiltered
11. concentrationthe solvent concentrated in vacuo to a brown solid
12. customThe brown solid was purified by trituration with ethyl acetate/hexane

ORD 기록

ord-0551e43310d848fe92423525aba078df

출처 데이터셋

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06894061B2