GB612115A - Process for the manufacture of quinoline compounds - Google Patents

Process for the manufacture of quinoline compounds

Info

Publication number
GB612115A
GB612115A GB2795045A GB2795045A GB612115A GB 612115 A GB612115 A GB 612115A GB 2795045 A GB2795045 A GB 2795045A GB 2795045 A GB2795045 A GB 2795045A GB 612115 A GB612115 A GB 612115A
Authority
GB
United Kingdom
Prior art keywords
hydroxyanilino
chloroquinoline
diethylaminomethyl
methoxyquinoline
methyl
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
GB2795045A
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
Priority to US576900A priority Critical patent/US2474820A/en
Application filed by Parke Davis and Co LLC filed Critical Parke Davis and Co LLC
Priority to GB2795045A priority patent/GB612115A/en
Publication of GB612115A publication Critical patent/GB612115A/en
Priority to MY5300057A priority patent/MY5300057A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4
    • C07D215/44—Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04—Heterocyclic 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
    • C07D219/08—Nitrogen atoms
    • C07D219/10—Nitrogen atoms attached in position 9
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings

Abstract

4-Amino substituted quinoline compounds are prepared by reacting in acid solution or in the form of an acid salt a 4-haloquinoline of the formula <FORM:0612115/IV(b)/1> either with an aminomethyl substituted aminophenol of the formula <FORM:0612115/IV(b)/2> or with the corresponding aminophenol of the formula <FORM:0612115/IV(b)/3> followed by treatment of the latter reaction product with formaldehyde and the corresponding amine of the formula <FORM:0612115/IV(b)/4> where Z is hydrogen, halogen, -CH, -COOH, -COO alkyl, alkyl or alkoxy, n is 1, 2 or 3, R is hydrogen, halogen, -OH or saturated or unsaturated alkyl radical containing 1-8 carbon atoms inclusive, R2 is a saturated or unsaturated or unsaturated alkyl radical containing 1-8 carbon atoms inclusive, and R1 and R2 taken together with -N may form a saturated heterocyclic ring system which may be alkyl substituted, and X is a chlorine or a bromine atom. The acids which may be present either as free acid, or as the salts are preferably the mineral acids or the lower fatty acids. Those specifically mentioned being hydrochloric, sulphuric, phosphoric, acetic propionic and butyric acids. Ring systems which are mentioned as being formed by R1 and R2 with nitrogen, include the pyrollidine, piperidine, morpholine and thiomorpholine rings. In a modification of the invention the aminomethyl substituted aminophenol may be used in the form of its acyl derivative, the reaction being carried out in acid solution. The various phases of the invention are illustrated by a large number of examples. The following compounds are the products obtained: (1) 4 - (31 - diethylaminomethyl - 41 - hydroxyanilino) - 7 - chloroquinoline; (2) 4 - (31 - N-piperidylmethyl - 41 - hydroxyanilino) - 7-chloroquinoline; (3) 4 - (31 - N - a - methylpiperidylmethyl - 41 - hydroxyanilino) - 7-chloroquinoline; (4) 4 - (31 - N - morpholinyl methyl - 41 - hydroxyanilino) - 7 - chloroquinoline; (5) 4 - (31 - diethylaminomethyl-41-hydroxy - 51 - allylanilino) - 7 - chloroquinoline; (6) 4 - (31 - diethylaminomethyl - 41 - hydroxyanilino) - 7 - bromoquinoline; (7) 4 - (31 - N-thiomorpholenylmethyl - 41 - hydroxyanilino)-7 - chloroquinoline; (8) 4 - (31 - N - piperazinomethyl - 41 - hydroxyanilino) - 7 - chloroquinoline; (9) 4 - (31 - di - n - butylaminomethyl-41 - hydroxyanilino - 7 - chloroquinoline; (10) 4 - (31 - diethylaminomethyl - 41 - hydroxyanilino) - 6 : 7 - dimethylquinoline; (11) 4 - (31-N - piperidylmethyl - 41 - hydroxyanilino) - 6-methylquinoline; (12) 4 - (31 - N - morpholinylmethyl - 41 - hydroxyanilino) - 6 - methylquinoline; (13) 4 - (31 - N - piperidylmethyl - 41-hydroxyanilino) - 6 - methoxyquinoline; (14) 4 - (31 - N - morpholinylmethyl - 41 - hydroxyanilino) - methoxyquinoline; (15) 4 - (31 - diethylaminomethyl - 41 - hydroxyanilino) - 6-methoxyquinoline; (16) 4 - (31 - chloro - 51-diethylaminomethyl - 61 - hydroxyanilino) - 6-methoxyquinoline; (17) 3-carbethoxy - 4 - (31-N - piperdylmethyl - 41 - hydroxyanilino) - 6-methoxyquinoline; (18) 3 - methyl - 4 - (31 - diethylaminomethyl - 41 - hydroxyanilino) - 7-chloroquinoline; (19) 3 - methyl - 4 - (31 - N-piperidylmethyl - 41 - hydroxyanilino) - 7-chloroquinoline; (20) 3 - methyl - 4 - (31 - N-morpholinylmethyl - 41 - hydroxyanilino) - 7-chloroquinoline; (21) 4 - (31 - diethylaminomethyl - 41 - hydroxyanilino) - 5 - chloro - 8-methoxyquinoline; (22) 4 - (31 - diethylaminomethyl - 41 - hydroxyanilino) - 5 - methyl - 8-methoxyquinoline; (23) 2 - methyl - 4 - (31 - diethylaminomethyl - 41 - hydroxyanilino) - 6-methoxyquinoline; (24) 4 - (31 - diethylaminomethyl - 41 - hydroxyanilino) - 6 - hydroxyquinoline; (25) 4 - (31 - hydroxy - 41 - diethylaminomethylanilino) - 7 - cyanoquinoline; (26) 4 - (31 - ethylaminomethyl - 41 - hydroxyanilino)-7 - chloroquinoline; (27) 3 - methyl - 4 - (31 - n-butylaminomethyl - 41 - hydroxyanilino) - 7-chloroquinoline. Aminomethylaminophenols used above may be prepared by condensation of primary or secondary amines with formaldehyde and acylaminophenols having at least one unsubstituted position ortho or para to the phenolic hydroxyl group and hydrolysing the resulting N-substituted aminoethyl acylaminophenols. They may also be prepared by the catalytic or nascent hydrogen reduction of aminomethyl nitrophenols. Specification 584,917 is referred to.
GB2795045A 1945-02-08 1945-10-23 Process for the manufacture of quinoline compounds Expired GB612115A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US576900A US2474820A (en) 1945-02-08 1945-02-08 Quinoline compounds and process of making same
GB2795045A GB612115A (en) 1945-10-23 1945-10-23 Process for the manufacture of quinoline compounds
MY5300057A MY5300057A (en) 1945-10-23 1953-12-30 Improvements in or relating to fumigating compositions

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2795045A GB612115A (en) 1945-10-23 1945-10-23 Process for the manufacture of quinoline compounds

Publications (1)

Publication Number Publication Date
GB612115A true GB612115A (en) 1948-11-09

Family

ID=10267882

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2795045A Expired GB612115A (en) 1945-02-08 1945-10-23 Process for the manufacture of quinoline compounds

Country Status (2)

Country Link
GB (1) GB612115A (en)
MY (1) MY5300057A (en)

Cited By (3)

* 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
EP0027679A2 (en) * 1979-10-18 1981-04-29 Warner-Lambert Company Substituted-5-((7-chloro-4-quinolinyl)amino)-3-(amino-methyl)-(1,1'-biphenyl)-2-ol compounds; processes for their production; and pharmaceutical compositions containing the compounds
EP0222839A1 (en) * 1985-05-17 1987-05-27 The Australian National University Antimalarial compounds

Cited By (5)

* 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
EP0027679A2 (en) * 1979-10-18 1981-04-29 Warner-Lambert Company Substituted-5-((7-chloro-4-quinolinyl)amino)-3-(amino-methyl)-(1,1'-biphenyl)-2-ol compounds; processes for their production; and pharmaceutical compositions containing the compounds
EP0027679A3 (en) * 1979-10-18 1981-07-15 Warner-Lambert Company Substituted-5-((7-chloro-4-quinolinyl)amino)-3-(amino-methyl)-(1,1'-biphenyl)-2-ol compounds; processes for their production; pharmaceutical compositions containing the compounds; intermediate compounds for use in said processes; and production of the intermediates
EP0222839A1 (en) * 1985-05-17 1987-05-27 The Australian National University Antimalarial compounds
EP0222839A4 (en) * 1985-05-17 1988-11-09 Univ Australian Antimalarial compounds.

Also Published As

Publication number Publication date
MY5300057A (en) 1953-12-31

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