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Cas Database

100009-76-5

100009-76-5

Identification

  • Product Name:1-(2'-methoxycarbonyl-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline

  • CAS Number: 100009-76-5

  • EINECS:

  • Molecular Weight:383.401

  • Molecular Formula:C21H21NO6

  • HS Code:

  • Mol File:100009-76-5.mol

Synonyms:1-(2'-methoxycarbonyl-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline

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    Relevant articles and documentsAll total 2 Articles be found

    The structure of 2,3-dihydromenisporphine and the synthesis of dauriporphine, oxoisoaporphine alkaloids from Menispermum dauricum DC

    Kunitomo,Kaede,Satoh

    , p. 2778 - 2782 (2007/10/02)

    -

    A novel approach to oxoisoaporphine alkaloids via regioselective metalation of alkoxy isoquinolines

    Melzer, Benedikt C.,Bracher, Franz

    , p. 1564 - 1571 (2017/08/14)

    Oxoisoaporphine alkaloids are conveniently prepared via direct ring metalation of alkoxy-substituted isoquinolines at C-1, followed by reaction with iodine. Subsequent Suzuki cross-coupling of the resulting 1-iodoisoquinolines to methyl 2-(isoquinolin-1-y

    Process route upstream and downstream products

    Process route

    5-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid methyl ester
    1146214-81-4

    5-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid methyl ester

    1-iodo-5,6,7-trimethoxyisoquinoline

    1-iodo-5,6,7-trimethoxyisoquinoline

    1-(2'-methoxycarbonyl-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline
    100009-76-5

    1-(2'-methoxycarbonyl-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline

    Conditions
    ConditionsYield
    With tetrakis(triphenylphosphine) palladium(0); potassium carbonate;Intetrahydrofuran; water;for 24h; Reflux; Inert atmosphere;
    65%
    2-(2,3,4-trimethoxyphenyl)ethylamine
    3937-16-4

    2-(2,3,4-trimethoxyphenyl)ethylamine

    1-(2'-methoxycarbonyl-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline
    100009-76-5

    1-(2'-methoxycarbonyl-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline

    Conditions
    ConditionsYield
    Multi-step reaction with 5 steps
    1: 86.9 percent / 10 percent NaOH / diethyl ether / 1 h / 0 °C
    2: 90.2 percent / POCl3 / toluene / 2.5 h / 120 - 140 °C / Heating
    3: 89.2 percent / dimethylformamide / 5 h / 180 °C
    4: 40 percent ethanolic KOH / 40 h / Heating
    5: diethyl ether; methanol
    With potassium hydroxide; sodium hydroxide; trichlorophosphate;Inmethanol; diethyl ether; N,N-dimethyl-formamide; toluene;
    2-bromo-4-methoxybenzoic acid
    74317-85-4

    2-bromo-4-methoxybenzoic acid

    1-(2'-methoxycarbonyl-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline
    100009-76-5

    1-(2'-methoxycarbonyl-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline

    Conditions
    ConditionsYield
    Multi-step reaction with 6 steps
    1: SOCl2
    2: 86.9 percent / 10 percent NaOH / diethyl ether / 1 h / 0 °C
    3: 90.2 percent / POCl3 / toluene / 2.5 h / 120 - 140 °C / Heating
    4: 89.2 percent / dimethylformamide / 5 h / 180 °C
    5: 40 percent ethanolic KOH / 40 h / Heating
    6: diethyl ether; methanol
    With potassium hydroxide; sodium hydroxide; thionyl chloride; trichlorophosphate;Inmethanol; diethyl ether; N,N-dimethyl-formamide; toluene;
    2-Brom-4-methoxybenzoesaurechlorid
    88741-40-6

    2-Brom-4-methoxybenzoesaurechlorid

    1-(2'-methoxycarbonyl-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline
    100009-76-5

    1-(2'-methoxycarbonyl-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline

    Conditions
    ConditionsYield
    Multi-step reaction with 5 steps
    1: 86.9 percent / 10 percent NaOH / diethyl ether / 1 h / 0 °C
    2: 90.2 percent / POCl3 / toluene / 2.5 h / 120 - 140 °C / Heating
    3: 89.2 percent / dimethylformamide / 5 h / 180 °C
    4: 40 percent ethanolic KOH / 40 h / Heating
    5: diethyl ether; methanol
    With potassium hydroxide; sodium hydroxide; trichlorophosphate;Inmethanol; diethyl ether; N,N-dimethyl-formamide; toluene;
    1-(2'-cyano-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline
    100009-78-7

    1-(2'-cyano-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline

    1-(2'-methoxycarbonyl-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline
    100009-76-5

    1-(2'-methoxycarbonyl-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline

    Conditions
    ConditionsYield
    Multi-step reaction with 2 steps
    1: 40 percent ethanolic KOH / 40 h / Heating
    2: diethyl ether; methanol
    With potassium hydroxide;Inmethanol; diethyl ether;
    1-(2'-bromo-4'-methoxyphenyl)-5,6,7-trimethoxy-3,4-dihydroisoquinoline
    100009-80-1

    1-(2'-bromo-4'-methoxyphenyl)-5,6,7-trimethoxy-3,4-dihydroisoquinoline

    1-(2'-methoxycarbonyl-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline
    100009-76-5

    1-(2'-methoxycarbonyl-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline

    Conditions
    ConditionsYield
    Multi-step reaction with 3 steps
    1: 89.2 percent / dimethylformamide / 5 h / 180 °C
    2: 40 percent ethanolic KOH / 40 h / Heating
    3: diethyl ether; methanol
    With potassium hydroxide;Inmethanol; diethyl ether; N,N-dimethyl-formamide;
    N-(2',3',4'-trimethoxyphenethyl)-2-bromo-4-methoxybenzamide
    100009-74-3

    N-(2',3',4'-trimethoxyphenethyl)-2-bromo-4-methoxybenzamide

    1-(2'-methoxycarbonyl-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline
    100009-76-5

    1-(2'-methoxycarbonyl-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline

    Conditions
    ConditionsYield
    Multi-step reaction with 4 steps
    1: 90.2 percent / POCl3 / toluene / 2.5 h / 120 - 140 °C / Heating
    2: 89.2 percent / dimethylformamide / 5 h / 180 °C
    3: 40 percent ethanolic KOH / 40 h / Heating
    4: diethyl ether; methanol
    With potassium hydroxide; trichlorophosphate;Inmethanol; diethyl ether; N,N-dimethyl-formamide; toluene;
    5,6,7-trimethoxyisoquinoline
    36982-71-5

    5,6,7-trimethoxyisoquinoline

    1-(2'-methoxycarbonyl-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline
    100009-76-5

    1-(2'-methoxycarbonyl-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline

    Conditions
    ConditionsYield
    Multi-step reaction with 2 steps
    1.1: 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex / tetrahydrofuran; toluene / 4 h / 25 °C / Schlenk technique; Inert atmosphere
    1.2: 1 h / 0 - 25 °C / Schlenk technique; Inert atmosphere
    2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 24 h / Reflux; Inert atmosphere
    With tetrakis(triphenylphosphine) palladium(0); 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex; potassium carbonate;Intetrahydrofuran; water; toluene;2.1: |Suzuki Coupling;
    5-Methoxy-2-(5,6,7-trimethoxy-isoquinolin-1-yl)-benzoic acid
    100009-77-6

    5-Methoxy-2-(5,6,7-trimethoxy-isoquinolin-1-yl)-benzoic acid

    1-(2'-methoxycarbonyl-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline
    100009-76-5

    1-(2'-methoxycarbonyl-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline

    Conditions
    ConditionsYield
    Inmethanol; diethyl ether;Yield given;
    5-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid methyl ester
    1146214-81-4

    5-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid methyl ester

    1-iodo-5,6,7-trimethoxyisoquinoline

    1-iodo-5,6,7-trimethoxyisoquinoline

    1-(2'-methoxycarbonyl-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline
    100009-76-5

    1-(2'-methoxycarbonyl-4'-methoxyphenyl)-5,6,7-trimethoxyisoquinoline

    Conditions
    ConditionsYield
    With tetrakis(triphenylphosphine) palladium(0); potassium carbonate;Intetrahydrofuran; water;for 24h; Reflux; Inert atmosphere;
    65%

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