GB603533A - Process for the manufacture of acridine compounds - Google Patents

Process for the manufacture of acridine compounds

Info

Publication number
GB603533A
GB603533A GB2795245A GB2795245A GB603533A GB 603533 A GB603533 A GB 603533A GB 2795245 A GB2795245 A GB 2795245A GB 2795245 A GB2795245 A GB 2795245A GB 603533 A GB603533 A GB 603533A
Authority
GB
United Kingdom
Prior art keywords
acridine
methoxy
chloro
hydroxyanilino
hydroxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB2795245A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Parke Davis and Co LLC
Original Assignee
Parke Davis and Co LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Parke Davis and Co LLC filed Critical Parke Davis and Co LLC
Priority to GB2795245A priority Critical patent/GB603533A/en
Publication of GB603533A publication Critical patent/GB603533A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D219/00Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • C07D219/08Nitrogen atoms
    • C07D219/10Nitrogen atoms attached in position 9

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Materials For Photolithography (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)

Abstract

9-Amino substituted acridine compounds of the formula <FORM:0603533/IV(b)/1> are prepared by reacting a 9-halo or a 9-aryloxy acridine compound with an aminomethylaminophenol under acidic conditions. The phenol and the acridine compound are such as have substituents in appropriate positions such as to give a final product of the formula above. The acidic conditions comprise the use of either an acid addition salt of the aminomethylaminophenol or the use of an aqueous acidic or a non-aqueous phenolic medium. In the above formula R and R1 are hydrogen, lower alkyl or lower alkoxy. R2 is hydrogen, halogen or -CN, R3 is hydrogen or halogen, the group <FORM:0603533/IV(b)/2> or a hydroxy, lower alkyl, lower alkylene, lower alkoxy, or a phenyl radical. R4 is hydrogen or a saturated or unsaturated alkyl radical containing from 1-8 carbon atoms, and R5 is a saturated or unsaturated alkyl radical containing from 1-8 carbon atoms. R4 and R5 taken together with -N< may form a saturated keterocyclic ring system such as pyrollidine, piperidine or morpholine. The reaction is carried out in an aqueous or aqueous-organic, or organic solvent. Solvents mentioned include methanol, ethanol, propanol, dioxane, acetone and acetic acid. Instead of using the free amino phenol, there may be employed the corresponding acylamino compound. The acyl group is split off under the acidic conditions of the condensation. Examples are given of the preparation of the compounds of the invention by refluxing together in one or other of the solvents mentioned above the appropriate aminomethylaminophenol and the appropriate acridine compound. Compounds whose preparation is described in detail in the particular examples are (1) 2-methoxy-6-chloro-9 - (31-diethylaminomethyl - 41 - hydroxyanilino) acridine; (2) 2-methoxy-6-chloro-(31-hydroxy-41 - diethylamino - methylanilino) acridine; (3) 2 - methoxy - 6 - chloro - 9 - (31-ethylaminomethyl-41-hydroxyanilino) acridine; (4) 9-(31-diethylaminomethyl-41-hydroxyanilino) acridine; (5) 2 - methoxy - 6 - chloro - 9 - (31-di - n - butylaminomethyl - 41 - hydroxyanilino) acridine; (6) 2 - methoxy-6-chloro-9-(31-di-n-hexylaminomethyl-41 -hydroxyanilino) acridine; (7) 2 : 3-dimethyl-6-chloro-9-(31-diethylaminomethyl-41-hydroxy anilino) acridine; (8) 2 - methoxy - 6 - chloro - 9 - (31 - diallylaminomethyl - 41 - hydroxyanilino) acridine; (9) 2 - methoxy - 6 - cyano - 9 - (31 - N a : a 1 - dimethylpyrrolidylmethyl - 41 - hydroxy - anilino) acridine; (10) 2 - methoxy - 6 - chloro - 9 - (31-N-piperidylmethyl-41-hydroxyanilino) acridine; (11) 2-methoxy-6-chloro-9-(21-hydroxy - 31 - diethylaminomethyl - 51 - tert. - butylanilino) acridine; (12) 2 - methoxy - 6 - bromo - 9 - (31 - N - morpholinylmethyl - 41 - hydroxyanilino) acri - dine; (13) 2-methoxy-6-chloro-9-(21-hydroxy-31-diethylaminomethyl -51-phenylanilino) acridine; (14) 2-methoxy-6-chloro-9-(31-diethylaminomethyl - 41 - hydroxy - 5 - allylanilino) acri - dine; (15) 2 : 3-dimethoxy-9-(21-41-dihydroxy-51 - n - propylaminomethyl) acridine; (16) 2 - methoxy-6-chloro-9-(31-N-piperidylmethyl-41-hydroxy - 51 - allylanilino) acridine; (17) 2 - methoxy-6-chloro-9-(31-diallylaminomethyl-41-hydroxy - 5 - allylanilino) acridine; (18) 2 - methoxy-6-chloro-9-(31-diethylaminomethyl-41-hydroxy - 61 - chloroanilino) acridine; (19) 2-methoxy-6-chloro-9-[31 : 51-bis-(diethylaminomethyl)-21-hydroxyanilino] acridine. The substitute acylaminophenols are prepared from the corresponding acylaminophenols by reacting them with formaldehyde and a secondary amine.ALSO:9-Amino-substituted acridine compounds of the formula <FORM:0603533/IV (c)/1> are prepared by reacting a 9-halo or a 9-aryloxy acridine compound with an aminomethylaminophenol under acidic conditions. The phenol and the acridine compound are such as have substituents in appropriate positions such as to give a final product of the formula above. The acidic conditions comprise the use of either an acid addition salt of the aminomethylaminophenol or the use of an aqueous acidic or a non-aqueous phenolic medium. In the above formula R and R1 are hydrogen, lower alkyl or lower alkoxy. R2 is hydrogen, halogen or -CN, R3 is hydrogen or halogen, the group <FORM:0603533/IV (c)/2> or a hydroxy, lower alkyl, lower alkylene, lower alkoxy, or a phenyl radical. R4 is hydrogen or a saturated or unsaturated alkyl radical containing from 1-8 carbon atoms, and R5 is a saturated or unsaturated alkyl radical containing from 1-8 carbon atoms. R4 and R5 taken together with -N may form a saturated heterocyclic ring system such as pyrollidine, piperidine or morpholine. The reaction is carried out in an aqueous, or aqueous-organic, or organic solvent. Solvents mentioned include methanol, ethanol, propanol, dioxane, acetone and acetic acid. Instead of using the free amino phenol, there may be employed the corresponding arylamino compound. The aryl group is split off under the acidic conditions of the condensation. Examples are given of the preparation of the compounds of the invention by refluxing together in one or other of the solvents mentioned above the appropriate aminomethylaminophenol and the appropriate acridine compound. Compounds whose preparation is described in detail in the particular examples are (1) 2-methoxy-6-chloro-9-(31-diethyl-aminomethyl-41 -hydroxyanilino) acridine; (2) 2-methoxy-6-chloro-(31-hydroxy-41 - diethylamino - methylanilino) acridine; (3) 2-methoxy-6-chloro-9-(31-ethylaminomethyl-41 -hydroxyanilino) acridine; (4) 9 - (31-diethylaminomethyl-41-hydroxyanilino) acridine; (5) 2-methoxy-6-chloro-9-(31-di-n-butylaminomethyl - 41 - hydroxyanilino) acridine; (6) 2-methoxy-6-chloro-9-(31-di-n-hexylaminomethyl-41 -hydroxyanilino) acridine; (7) 2 : 3-dimethyl-6-chloro-9-(31-diethylaminomethyl-41-hydroxy anilino) acridine; (8) 2-methoxy-6-chloro-9-(31 - diallylaminomethyl - 41 - hydroxyanilino) acridine; (9) 2-methoxy-4-cyano-9-(31-N-dimethylpyrrolidylmethyl - 41 - hydroxyanilino) acridine; (10) 2-methoxy-6-chloro-9-(31-N-piperidylmethyl-41 -hydroxyanilino) acridine; (11) 2-methoxy - 6 - chloro - 9 - (21-hydroxy-31-diethylaminomethyl-51-tert. -butylanilino) acridine; (12) 2 - methoxy - 6 - bromo - 9 - (31 - N - morpholinylmethyl - 41 - hydroxyanilino) acridine; (13) 2-methoxy-6-chloro-9-(21-hydroxy-31 - diethylaminomethyl - 51 - phenylanilino) acridine; (14) 2-methoxy-6-chloro-9-(31-diethylaminomethyl - 41 - hydroxy - 5 - allylanilino) acridine; (15) 2 : 3-dimethoxy-9-(21-41-dihydroxy - 51 - n - propylaminomethyl) acridine; (16) 2-methoxy-6-chloro-9-(31-N-piperidyl-methyl-41-hydroxy -51-allylanilino) acridine; (17) 2-methoxy-6-chloro-9-(31-diallylaminomethyl-41-hydroxy -5-allkylanilino) acridine; (18) 2-methoxy-6-chloro-9-(31-diethylamino-methyl-41-hydroxy -61-chloroanilino) acridine; (19) 2-methoxy-6-chloro-9-[31 : 51-bis-(diethylaminomethyl)-21-hydroxyanilino] acridine.
GB2795245A 1945-10-23 1945-10-23 Process for the manufacture of acridine compounds Expired GB603533A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2795245A GB603533A (en) 1945-10-23 1945-10-23 Process for the manufacture of acridine compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2795245A GB603533A (en) 1945-10-23 1945-10-23 Process for the manufacture of acridine compounds

Publications (1)

Publication Number Publication Date
GB603533A true GB603533A (en) 1948-06-17

Family

ID=10267908

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2795245A Expired GB603533A (en) 1945-10-23 1945-10-23 Process for the manufacture of acridine compounds

Country Status (1)

Country Link
GB (1) GB603533A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2157884A1 (en) * 1971-10-19 1973-06-08 Astra Ab

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2157884A1 (en) * 1971-10-19 1973-06-08 Astra Ab

Similar Documents

Publication Publication Date Title
GB1065920A (en) Substituted benzoxazinones and a process for their preparation
GB957797A (en) Method for making 2,4-diamino-5-arylmethylpyrimidines and intermediates therefor
GB603533A (en) Process for the manufacture of acridine compounds
GB913866A (en) Improvements in or relating to amino-norcamphane compounds
US2569415A (en) Imidazolines
GB1047061A (en) Polymers and a process for the preparation thereof
GB1022741A (en) Process for the production of ú­-amino-aryl aldehydes
GB959203A (en) Indole derivatives and salts thereof
US3470174A (en) Cyclodiene carbox amides
GB861900A (en) New amino ethers and their process of preparation
GB894428A (en) Process for the manufacture of basically substituted phthalazines
GB799366A (en) Process for the preparation of acridine compounds
US3818037A (en) 3-methylene-6-nitro-n-substituted isoindolones-(1)
GB1131467A (en) New basic derivatives of benzoxazine and methods for their production
GB632277A (en) Improvements in or relating to the preparation of derivatives of phenthiazine
Kelarev et al. Synthesis and properties of azoles and their derivatives. 35. Synthesis of certain azoles containing sterically hindered phenol residues
GB606158A (en) The manufacture of substituted benzhydryl ethers
GB612115A (en) Process for the manufacture of quinoline compounds
GB761796A (en) New quinoline derivatives
GB1067626A (en) 3-aminoalkyl-4-alkyl-coumarin derivatives and process for the manufacture thereof
GB705878A (en) Heterocyclic nitrogen compounds and methods for obtaining the same
GB793088A (en) Acridan derivatives
GB646946A (en) Process of producing aromatic sulfonamido pyrimidines
ES238791A1 (en) A procedure for the obtaining of 2-acilo4-4aminofenol-unsaturated etheries (Machine-translation by Google Translate, not legally binding)
GB826323A (en) New triazine derivatives and a process for their production