2-[6′-(4′′-chlorophenyl)-7′-methoxy-3′,4′-dihydro-1H-quinolin-2′-one-1′-yl]acetic acid

Base Information

Chemical Name:2-[6′-(4′′-chlorophenyl)-7′-methoxy-3′,4′-dihydro-1H-quinolin-2′-one-1′-yl]acetic acid
CAS No.:1224927-76-7
Molecular Formula:C₁₈H₁₆ClNO₄
Molecular Weight:345.782
Hs Code.:

Synonyms:2-[6′-(4′′-chlorophenyl)-7′-methoxy-3′,4′-dihydro-1H-quinolin-2′-one-1′-yl]acetic acid

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Chemical Property of 2-[6′-(4′′-chlorophenyl)-7′-methoxy-3′,4′-dihydro-1H-quinolin-2′-one-1′-yl]acetic acid

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Technology Process of 2-[6′-(4′′-chlorophenyl)-7′-methoxy-3′,4′-dihydro-1H-quinolin-2′-one-1′-yl]acetic acid

There total 5 articles about 2-[6′-(4′′-chlorophenyl)-7′-methoxy-3′,4′-dihydro-1H-quinolin-2′-one-1′-yl]acetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

: 1224927-82-5
tert-butyl 2-[6′-(4′′-chlorophenyl)-7′-methoxy-3′,4′-dihydro-1H-quinolin-2′-one-1′-yl]acetate

: 1224927-76-7
2-[6′-(4′′-chlorophenyl)-7′-methoxy-3′,4′-dihydro-1H-quinolin-2′-one-1′-yl]acetic acid

Guidance literature:: With trifluoroacetic acid; In dichloromethane; for 120h; Inert atmosphere; Reflux;
DOI:10.1021/acs.joc.8b01910

Reference yield:

: 103986-96-5
methyl (E)-3-(4′-methoxy-2′-nitrophenyl)acrylate

: 1224927-76-7
2-[6′-(4′′-chlorophenyl)-7′-methoxy-3′,4′-dihydro-1H-quinolin-2′-one-1′-yl]acetic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: hydrogen / 24 h / 20 °C / 1875.19 Torr / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 20 °C / Inert atmosphere

2.2: 1.5 h / Inert atmosphere

3.1: iron(III) chloride; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide; N-Bromosuccinimide / toluene / 24 h / 20 - 40 °C / Inert atmosphere

4.1: sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; N,N-dimethyl-formamide / 24 h / 120 °C / Inert atmosphere

5.1: trifluoroacetic acid / dichloromethane / 120 h / Inert atmosphere; Reflux

With iron(III) chloride; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; sodium hydride; sodium hydrogencarbonate; trifluoroacetic acid; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide; In dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil; 4.1: |Suzuki-Miyaura Coupling;
DOI:10.1021/acs.joc.8b01910

Reference yield:

: 96-96-8
4-methoxy-2-nitroaniline

: 1224927-76-7
2-[6′-(4′′-chlorophenyl)-7′-methoxy-3′,4′-dihydro-1H-quinolin-2′-one-1′-yl]acetic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: toluene-4-sulfonic acid; palladium diacetate / methanol / 1.5 h / 60 °C / Inert atmosphere

2.1: hydrogen / 24 h / 20 °C / 1875.19 Torr / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 20 °C / Inert atmosphere

3.2: 1.5 h / Inert atmosphere

4.1: iron(III) chloride; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide; N-Bromosuccinimide / toluene / 24 h / 20 - 40 °C / Inert atmosphere

5.1: sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; N,N-dimethyl-formamide / 24 h / 120 °C / Inert atmosphere

6.1: trifluoroacetic acid / dichloromethane / 120 h / Inert atmosphere; Reflux

With iron(III) chloride; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; palladium diacetate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; trifluoroacetic acid; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil; 5.1: |Suzuki-Miyaura Coupling;
DOI:10.1021/acs.joc.8b01910