59 45 h 5 06 n 29 51 6 2 methylpropyl 6h imidazo 4 5 c tetrazolo 1 5 a quinoline 0 2 g 0 75 mmole example 8 triphenylphosphine 0 4 g 1 5 mmole and 1 2 dichlorobenzene 5 ml were combined and heated at reflux overnight the reaction mixture was concentrated under vacuum then diluted with cyclohexane 25 ml the resulting precipitate was isolated by filtration washed with cyclohexane then dried to provide 1 2 methylpropyl n triphenylphosphinyl 1h imidazo 4 5 c quinolin 4 amine as a solid m p 209 210 u00b0 c analysis calculated for c 32 h 29 n 4 p c 76 78 h 5 84 n 11 19 found c 76 03 h 5 87 n 11 09 triphenylphosphine 4 5 g 17 0 mmole was added to a mixture of u03b1 u03b1 dimethyl 6h imidazo 4 5 c tetrazolo 1 5 a quinoline 6 ethanol 2 4 g 8 5 mmole example 9 and 1 2 dichlorobenzene the reaction mixture was heated at reflux for 3 hrs then concentrated under vacuum the residue was combined with methanol 400 ml and hydrochloric acid 50 ml of 0 5 n then heated on a steam bath for 2 hours the resulting precipitate was isolated by filtration then washed with ether the solid was dissolved in water and the solution was made basic with 10 sodium hydroxide after stirring for 30 minutes the reaction mixture was filtered the collected solid was rinsed with water and ether then recrystallized from n n dimethylformamide ethanol to provide about 1 g of 4 amino u03b1 u03b1 dimethyl 1h imidazo 4 5 c quinoline 1 ethanol as a solid m p 271 273 u00b0 c analysis calculated.