Patent GB-1327311-A (GB)
Title: Tetrazolo 1,5-a- quinoline agents for the control of plant- pathogenic organisms
IPC: C07D487/04
Filed: 1971-07-05
Abstract: 1327311 Quinolines; tetrazoloquinolines ELI LILLY & CO 5 July 1971 [8 July 1970] 31341/71 Heading C2C [Also in Division A5] Example 1: 2-chloro-6-ethyl-4-methylquinoline is prepared by reacting 6-ethyl-4-methylcarbostyril and phosphorus oxychloride. Example 2: 2,4-dichloro-3,8-dimethylquinoline is prepared by reacting 3,8-dimethyl- 4-hydroxy-carbostyril with phosphoryl chloride. Example 3: 2-chloro-8-methylquinoline is prepared by reaction of 1,8-dimethylcarbostyril, phosphorus oxychloride and phosphorus pentachloride. Example 4: 9-methyltetrazolo (1,5-a) quinoline is prepared by reacting 2-chloro-8- methyl-quinoline with sodium azide. Example 5: 9-(bromomethyl) tetrazolo (1,5-a) quinoline is prepared by reacting 9-methyltetrazolo (1,5-a) quinoline with N-bromosuccinimide.  Example 7: 9 - (hydroxymethyl) tetrazolo (1,5-a) quinoline is prepared by reacting 9- (bromomethyl) tetrazolo (1,5-a) quinoline with water. Example 8: 9 - formyltetrazolo (1,5-a) quinoline is prepared by oxidation of 9-(hydroxymethyl) tetrazolo (1,5-a) quinoline. Example 9: 5 - (methoxymethyl) tetrazolo (1,5-a) quinoline is prepared by reacting 5- (bromomethyl) tetrazolo (1,5-a) quinoline with sodium + methanol. Example 10: 9-nitrotetrazolo (1,5-a) quinoline is prepared by reacting 2-chloro-8-nitroquinoline with sodium azide. Example 11: 9-aminotetrazolo (1,5-a) quinoline is prepared by reacting 9-nitrotetrazolo (1,5-a) quinoline with hydrogen. Example 12: 9-acetamidotetrazolo (1,5-a) quinoline is prepared by reacting 9-aminotetrazolo (1,5-a) quinoline with acetic anhydride. Example 13: 5-morpholinotetrazolo (1,5-a) quinoline is prepared by reacting 5-chlorotetrazolo (1,5-a) quinoline with morpholine. Example 14: 3,4-dihydro-2-hydroazinoquinoline is prepared by reacting 3,4-dihydrothiocarbostyril with hydrazine. Example 17: 4-chlorotetrazolo (1,5-a) quinoline is prepared by reacting 4,5-dichloro-4,5- dihydrotetrazolo (1,5-a) quinoline in triethyl amine + ethanol. Example 18: 9-aminotetrazolo (1,5-a) quinoline, hydrochloride salt is prepared from 9- amino-tetrazolo (1,5-a) quinoline and anhydrous hydrochloric acid. Examples 19-67: the following compounds are prepared by similar methods to those above: Tetrazolo (1,5-a) quinoline, m.p., 156 C. 9-Chlorotetrazolo (1,5-a) quinoline, m.p., 195-200 C. 5-((Ethylamino) methyl) tetrazolo (1,5-a) quinoline, m.p., 118 C. 9-(Methoxymethyl) tetrazolo (1,5-a) quinoline, m.p., 160-61 C. 5-Vinyltetrazolo (1,5-a) quinoline. 9-(Ethoxymethyl) tetrazolo (1,5-a) quinoline, m.p., 176-77 C. 9-Fluoro-5-methyltetrazolo (1,5-a) quinoline, m.p., 212-13 C. 9-Bromo-5-methyltetrazolo (1,5-a) quinoline, m.p., 185-86 C. 7-Ethynyltetrazolo (1,5-a) quinoline. 5-Ethyltetrazolo (1,5-a) quinoline, m.p., 134- 35 C. 7-Chlorotetrazolo (1,5-a) quinoline, m.p., 221-22C. 5-Chlorotetrazolo (1,5-a) quinoline, m.p., 148 C. 5-(Aminomethyl) tetrazolo (1,5-a) quinoline. 5-Azidotetrazolo (1,5-a) quinoline, m.p., 185C. 8-Methyltetrazolo (1,5-a) quinoline, m.p., 143-44 C. 5-Methyltetrazolo (1,5-a) quinoline, m.p., 212-13 C. 5-Iodotetrazolo (1,5-a) quinoline. 5-(Bromomethyl) tetrazolo (1,5-a) quinoline, m,p., 184-85 C. 5-Cyanotetrazolo (1,5-a) quinoline, m.p., 232-35 C. 9-(Cyanomethyl) tetrazolo (1,5-a) quinoline, m.p., 221-22 C.  9-n-Propyltetrazolo (1,5-a) quinoline. 5-Chloro-4-methyltetrazolo (1,5-a) quinoline, m.p., 157-58 C. 5-(Hydroxymethyl) tetrazolo (1,5-a) quinoline, m.p., 249-51 C. 5-Chloro-4-ethyltetrazolo (1,5-a) quinoline, m.p., 113-14 C. 5-Chloro-9-((methylamino) methyl) tetrazolo (1,5-a) quinoline.  5-Chloro-7-methyltetrazolo (1,5-a) quinoline, m.p., 150-52 C. 5-Chloro-9-methyltetrazolo (1,5-a) quinoline, m.p., 176-78 C. 5,9-Dichlorotetrazolo (1,5-a) quinoline, m.p., 152-54 C. 8-((Isopropylamino) methyl) tetrazolo (1,5-a) quinoline. 5-Azido-7-methyltetrazolo (1,5-a) quinoline, m.p., 187-89 C. 5-Azido-9-chlorotetrazolo (1,5-a) quinoline, m.p., 170-71 C. 5-Chloro - 4,9 - dimethyltetrazolo (1,5-a) quinoline, m.p., 202-04 C. 5,9-Bis (chloromethyl) tetrazolo (1,5-a) quinoline. 5,9-Dichloro - 4 - methyltetrazolo (1,5-a) quinoline, m.p., 162-63 C. 5-Chloro - 9 - fluoro - 4 - methyltetrazolo (1,5-a) quinoline, m.p., 179-80 C. 5-Chloro - 9 - fluorotetrazolo (1,5-a) quinoline, m.p., 188-90 C. 5,6,9-Trichlorotetrazolo (1,5-a) quinoline. 5-Chloro - 9 - methyltetrazolo (1,5-a) quinoline, m.p., 210 C. 9-Ethyl - 5 - methyltetrazolo (1,5-a) quinoline, m.p., 110-11 C. 7-Ethyl - 5 - methyltetrazolo (1,5-a) quinoline, m.p., 160-62 C. 5-Morpholino - 7,9 - dichlorotetrazolo (1,5-a) quinoline. 7-Chloro - 5 - methyltetrazolo (1,5-a) quinoline, m.p., 183-84 C. 5-Methyl - 4 - chlorotetrazolo (1,5-a) quinoline, m.p., 204-05À5 C. 9-Chloro - 5 - methyltetrazolo (1,5-a) quinoline, m.p., 189-90 C. 9-(Iodomethyl) tetrazolo (1,5-a) quinoline. 7-Methyltetrazolo (1,5-a) quinoline, m.p., 163 C.  5-Bromotetrazolo (1,5-a) quinoline, m.p., 167-70 C. 5,9-Dimethyltetrazolo (1,5-a) quinoline, m.p., 196-97 C. 5,7-Dimethyltetrazolo (1,5-a) quinoline, m.p., 180 C. The tetrazoloquinoline compounds may possibly also exist as azido quinoline tautomers.