tion of the frans-acid began soon after the heating started. On cooling, 0.75 g. of product separated and was filtered off.n-Butyl N-carbamylmaleamate (IV. R = H, It' = n-C4H9). A mixture of 1184 g. of n-butanol, 560 g. (4.0 mol.) of Ilia, 8 g. of zinc chloride and 150 g. of petroleum ether (b.p. 60-70°) was refluxed at 85°until solution was complete. The solution was filtered and cooled, depositing 782 g. (92%) of the ester, m.p. 96-99°.Methyl N-carbamylfumaramate. Addition of 0.1 g. of aluminum chloride to 5.0 g. (0.036 mol.) of Ilia in 50 ml. of methanol caused an immediate exothermic reaction and precipitation of a quantitative yield of methyl JV-carbamylfumaramate, m.p. 228-230°.Copolymerization of Ilia with vinyl acetate. A solution of 10 g. (0.07 mol.) of Ilia, 25 ml. (0.27 mol.) of vinyl acetate and 0.1 g. of benzoyl peroxide in 194 ml. of dioxane was heated at 80°in a water bath for 6 hr. The polymer solution was poured into 1 1. of acetone. After filtration and drying, the polymer weighed 5.5 g. (17% conversion), was soluble in dimethylformamide and, with hydrolysis, in 10% aqueous sodium hydroxide, had intrinsic viscosity 0.13 and analyzed for 57.6% nitrogen. This analysis corresponds to a ratio of Ilia to vinyl acetate of 1:1.2 from a feed ratio of 1:3.8.Copolymerization of methyl N-carbamylmaleamate (IV. R = H, R' = CH,) with styrene. A mixture of 20 g. (0.192 mol.) of styrene, 20 g. (0.116 mol.) of IV and 0.8 g. of benzoyl peroxide in 40 g. of acetone was heated for 4.75 hr. in a water bath held at 70°. The clear solution, which still contained some undissolved IV, was poured into stirred methanol to precipitate the polymer. The precipitate was filtered off and dried overnight in an evacuated desiccator. The material was then triturated with methanol and again dried overnight in a vacuum desiccator. The product weighed 11.6 g. (29% conversion) and was soluble in dioxane and acetic acid. Nitrogen analysis (6.05, 6.05%) indicated that the monomer ratio (IV: styrene) in the polymer was 1:2.8 from a feed ratio of 1:1.65. The polymer had an intrinsic viscosity in dioxane of 0.11.

No abstract

A number of the title compounds are quite effective against Plasmodium berghei in mice. The most active members of this group are disubstituted and bear CFa groups or a combination of CF3 and halogen at positions 3 and 6.None of the 9-phenanthrenemethanols caused photosensitization in the test animals.Many of these compds are curative at 40 mg/kg and some at 20 mg/kg.

No abstract

and 5% methanol, v/v). Commercial Raney nickel was purchased from W.R. Grace Co. (no. 30). Silica gel was purchased from EM .5-Hydroxy-6-methoxy-4-methyl-8-nitroquinoline (2). 4-Methyl-5,6-dimethoxy-8-nitroquinoline4 (6.21 g, 25 mmol) was dissolved in EtOH (100 mL) containing concentrated HC1 (4.7 mL). The mixture was heated under reflux for 21 h, cooled to 10 °C, and filtered. The solid was washed with cold (10 °C) EtOH (18 mL), followed by petroleum ether (15 mL), and air-dried to yield 5.41 g (92%) of the title compound, mp 253-257 °C dec.Anal. (CuH10N2O4) C, , N.5-Chloro-6-methoxy-4-methyl-8-nitroquinoline (3). A solution of the above 5-hydroxyquinoline (5.25 g, 0.022 mol) in P0C13 (75 mL) was heated at 80 °C for 2 h. The reaction mixture was poured onto ice and basified with excess NH4OH. The tan solid was filtered to give 5.8 g of crude product. This material was purified via column chromatography over silica gel and eluted with CHC13. The fast-moving yellow band was collected and concentrated to give 3.9 g (69%) of the title compound, mp 167-169 °C. Anal. (CUH9C1N203) C, H, Cl, N.6-Methoxy-4-methyl-8-nitro-5-[3-(trifluoromethyl)phenoxyjquinoline (4a). To a solution of 3-(trifluoromethyl)phenol (4.1 g) in 2-ethoxyethanol (45 mL) containing KOH (1.37 g) was added the above 5-chloroquinoline (5.7 g, 0.023 mol). The mixture was heated at reflux for 8 h and allowed to cool overnight. The solid was filtered and washed well with cold EtOH to give 5.9 g (69%) of the title compound, mp 206-208 6C. An analytical