Acetic Acid → HCID 70091973, compound

A solution of 1,2-dihydro-3-[[5-methyl-1-(triphenylmethyl)-1H-imidazol-4-yl]methylene]-4(3H)-phenanthrenone (0.5 g) in a mixture of THF (15 ml), acetic acid (5 ml) and water (5 ml) was heated on a steam bath for 45 min. 0.5M Hydrochloric acid (25 ml) was added and the mixture was extracted with ether (2×15 ml; discarded). The aqueous solution was basified with solid potassium carbonate and the mixture was extracted with dichloromethane (3×15 ml). The dried extracts were evaporated and the residue (0.21 g) was dissolved in ethanol (25 ml) and hydrogenated at room temperature and atmospheric pressure over a stirred suspension of 10% palladium on carbon (0.05 g) for 1.5 h. The solution was filtered and the filtrate evaporated to give a gum which was purified by FCC eluting firstly with ethyl acetate and then with ethyl acetate/methanol (3:1) to give the free base of the title compound as a gum (0.13 g). This was dissolved in methanol (20 ml) containing maleic acid (50 mg) and the solution was evaporated to give a gum which on trituration with ether gave the title compound as a solid (0.11 g), m.p. 133°-134° .

1. temperaturewas heated on a steam bath for 45 min
2. extractionthe mixture was extracted with ether (2×15 ml; discarded)
3. extractionthe mixture was extracted with dichloromethane (3×15 ml)
4. customThe dried extracts were evaporated
5. dissolutionthe residue (0.21 g) was dissolved in ethanol (25 ml) and hydrogenated at room temperature
6. additionatmospheric pressure over a stirred suspension of 10% palladium on carbon (0.05 g) for 1.5 h
7. filtrationThe solution was filtered
8. customthe filtrate evaporated
9. customto give a gum which
10. customwas purified by FCC
11. washeluting firstly with ethyl acetate

ORD record

ord-0e39a3d03a724e259e25455f2108fa9b

Source dataset

uspto-grants-1992_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05116984