NEW BASICALLY SUBSTITUTED 1,2,3-BENZOTRIAZINE-4(3H)-ONE DERIVATIVES AND PROCESSES FOR THE PRODUCTION THEREOF

• Main Authors: RUDI BEYERLE, ADOLF STACHEL
• Format: Patent
• Language: English
• Published: 12.07.1972
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

1280941 3 - (y - Amino - # - hydroxy - propyl)- 1,2,3 - benzotriazin - 4(3H) - ones CASSELLA FARBWERKE MAINKUR AG 21 May 1970 [22 May 1969] 24679/70 Heading C2C Novel 3 - (y - amino - # - hydroxy - propyl)- 1,2,3 - benzotriazin - 4(3H) - ones of the general formula wherein R is a secondary aliphatic, cycloaliphatic or araliphatic amine radical having 2-10 carbon atoms or the radical of a 5, 6 or 7-ring membered heterocyclic optionally containing a further N, O or S heteroatom, R1 is a C 1-4 alkoxy group and n is 2 or 3, the alkoxy groups being in the 6 and 7 or 6, 7 and 8 positions, are prepared (a) by condensation of a 3 - (γ - halo - # - hydroxypropyl) - 1,2,3 - benzotriazin-4(3H)-one of the general formula wherein Hal is a chlorine or bromine atom, or the corresponding 3-(21,31-epoxypropyl) compound of the general formula with a secondary amine of the general formula RH; (b) by reaction of a 1,2,3-benzotriazin- 4(3H)-one of the general formula with a y-halo-#-hydroxy-propylamine of the general formula Hal-CH 2 -CH-(OH)-CH 2 R; and (c) by diazotization of a 2-amino-N-(γ- amino-#-hydroxy-propyl)-benzamide of the general formula 3 - (γ - Chloro - # - hydroxypropyl) - 6,7,8- trimethoxy - 1,2,3 - benzotriazin - 4(3H) - one is prepared by reaction of 3-chloro-1-aminopropanol-(2) hydrochloride with 2-nitro-3,4,5- trimethoxybenzoyl chloride, catalytic hydrogenation of the resulting 2-nitro-3,4,5-trimethoxy - N - (γ - chloro - # - hydroxy - propyl)- benzamide and diazotization of the resulting 2- amino - 3,4,5 - trimethoxy - N - (y - chloro - #- hydroxy - propyl) - benzamide hydrochloride. 3 - (21,31 - Epoxy - propyl) - 6,7,8 - trimethoxy- 1,2,3 - benzotriazin - 4(3H) - one is prepared by diazotization of 3,4,5-trimethoxyanthranilamide and reaction of the resulting 6,7,8-trimethoxy- 1,2,3 - benzotriazin - 4(3H) - one with epichlorohydrin. 2 - Amino - 3,4,5 - trimethoxy - N- (γ - morpholino - # - hydroxy - propyl) - benzamide dihydrochloride is prepared (a) by reaction of 2 - nitro - 3,4,5 - trimethoxy - N - (γ - chloro- B - hydroxy - propyl) - benzamide with morpholine and catalytic hydrogenation of the resulting 2 - nitro - 3,4,5 - trimethoxy - N - (γ- morpholino - # - hydroxy - propyl) - benzamide, (b) by reaction of 2-nitro-3,4,5-trimethoxybenzoyl chloride with N-(γ-amino-#-hydroxypropyl)-morpholine, followed by catalytic hydrogenation as in (a) and (c) by reaction of phosgene with 3,4,5-trimethoxy-2-amino-benzoic acid hydrochloride and reaction of the resulting 3,4,5 - trimethoxyisatoic anhydride with y-morpholino-#-hydroxy-propylamine.