GB645139A - Improved process for the production of isoquinoline derivatives - Google Patents

Improved process for the production of isoquinoline derivatives

Info

Publication number
GB645139A
GB645139A GB27069/47A GB2706947A GB645139A GB 645139 A GB645139 A GB 645139A GB 27069/47 A GB27069/47 A GB 27069/47A GB 2706947 A GB2706947 A GB 2706947A GB 645139 A GB645139 A GB 645139A
Authority
GB
United Kingdom
Prior art keywords
give
alkyl
ketone
isonitroso
dialkoxyphenyl
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
GB27069/47A
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.)
JOCZEF KISS
SERVITA GYOGYSZERYAR ES VEGYIP
Original Assignee
JOCZEF KISS
SERVITA GYOGYSZERYAR ES VEGYIP
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 JOCZEF KISS, SERVITA GYOGYSZERYAR ES VEGYIP filed Critical JOCZEF KISS
Publication of GB645139A publication Critical patent/GB645139A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
    • C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/18—Aralkyl radicals
    • C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1 - Substituted - 3 - alkyl - 6 : 7 - dialkoxyisoquinolines of the formula <FORM:0645139/IV (b)/1> wherein R1 and R2 denote alkyl radicals containing not less than 2 carbon atoms, R3 denotes an alkyl radical and R4 is an alkyl-, aryl-, or aralkyl radical which may be further substituted by alkoxy, alkylene-dioxy or hydroxy group or groups are prepared by condensing a 1 : 2-dialkoxybenzene with a fatty acid of at least 3 carbon atoms or a chloride or anhydride thereof in the presence of a Friedel-Craft catalyst such as boron trifluoride, treating the resulting 3 : 4-dialkoxyphenyl-alkylketone with nitrosifying agents, e.g. alkyl nitrites, to give 3 : 4 - dialkoxyphenyl - a - isonitroso - alkylketone, reducing the latter to the corresponding amino alcohol, acylating the amino group and finally condensing in the presence of dehydrating agents to give the desired isoquinoline derivative. Alternatively a 3 : 4-dioxyphenylalkylketone prepared from pyrocatechol monoalkyl ether may be treated with alkylating agents to give the dialkoxy compound or a pyrocatechol monoalkylether may be converted into a monoalkylether of 3 : 4-dioxyphenylalkylketone and alkylated to give the 3 : 4-dialkoxyphenyl-alkyl ketone. Also the reduction of the isonitroso ketone into the amine alcohol may be performed in two steps to give in the first place an amino ketone which may be reduced to the amino alcohol after the acylation step. In an example, 1 : 2-diethoxybenzene is treated with propionyl chloride in nitro-benzene in the presence of aluminium chloride to give 3 : 4-diethoxy-propiophenone, the latter compound is treated with isobutyl nitrite to give 3 : 4-diethoxyphenyl-a -isonitroso ethyl ketone, reduction of this compound with hydrogen in the presence of a platinum catalyst gives a -3 : 4-diethoxyphenyl-b -aminopropanol, which is benzoylated with benzoyl chloride to give a - 3 : 4 - diethoxyphenyl - b - benzoylaminopropanol, followed by treatment with phosphorus oxychloride in toluene to produce 1-phenyl - 3 - methyl - 6 : 7 - diethoxy - is phenyl-3-methyl-6 : 7-diethoxy-isoquinoline.
GB27069/47A 1946-10-22 1947-10-08 Improved process for the production of isoquinoline derivatives Expired GB645139A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HU645139X 1946-10-22

Publications (1)

Publication Number Publication Date
GB645139A true GB645139A (en) 1950-10-25

Family

ID=10979850

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27069/47A Expired GB645139A (en) 1946-10-22 1947-10-08 Improved process for the production of isoquinoline derivatives

Country Status (1)

Country Link
GB (1) GB645139A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2625743A1 (en) * 1988-01-08 1989-07-13 Sandoz Sa ISOQUINOLINE DERIVATIVES, THEIR PREPARATION AND THEIR USE
EP0491441A1 (en) * 1990-12-17 1992-06-24 Shell Internationale Researchmaatschappij B.V. Fungicidal isoquinoline derivatives
US5204471A (en) * 1991-08-10 1993-04-20 Bayer Aktiengesellschaft α-trifluoromethyl-substituted, saturated bicyclic amines
US5747506A (en) * 1993-11-05 1998-05-05 Novartis Ag Isoquinoline compounds, compositions containing them and their pharmaceutical uses

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2625743A1 (en) * 1988-01-08 1989-07-13 Sandoz Sa ISOQUINOLINE DERIVATIVES, THEIR PREPARATION AND THEIR USE
US4980359A (en) * 1988-01-08 1990-12-25 Sandoz Ltd. Isoquinoline derivatives and their use
BE1002730A3 (en) * 1988-01-08 1991-05-21 Sandoz Sa ISOQUINOLEIN DERIVATIVES, THEIR PREPARATION AND THEIR USE.
EP0491441A1 (en) * 1990-12-17 1992-06-24 Shell Internationale Researchmaatschappij B.V. Fungicidal isoquinoline derivatives
WO1992011242A1 (en) * 1990-12-17 1992-07-09 Shell Internationale Research Maatschappij B.V. Fungicidal isoquinoline derivatives
US5204471A (en) * 1991-08-10 1993-04-20 Bayer Aktiengesellschaft α-trifluoromethyl-substituted, saturated bicyclic amines
US5747506A (en) * 1993-11-05 1998-05-05 Novartis Ag Isoquinoline compounds, compositions containing them and their pharmaceutical uses

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