4-(3-chloro-phenyl)-6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-8-methoxy-1H-quinolin-2-one

Base Information

• Chemical Name: 4-(3-chloro-phenyl)-6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-8-methoxy-1H-quinolin-2-one
• CAS No.: 213389-54-9
• Molecular Formula: C₂₇H₂₁Cl₂N₃O₃
• Molecular Weight: 506.388

Synonyms:4-(3-chloro-phenyl)-6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-8-methoxy-1H-quinolin-2-one

Chemical Property of 4-(3-chloro-phenyl)-6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-8-methoxy-1H-quinolin-2-one

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Technology Process of 4-(3-chloro-phenyl)-6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-8-methoxy-1H-quinolin-2-one

There total 10 articles about 4-(3-chloro-phenyl)-6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-8-methoxy-1H-quinolin-2-one 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: 88.0%

1-methyl-1H-imidazole (616-47-7) + 6-(4-chloro-benzoyl)-4-(3-chloro-phenyl)-8-methoxy-1H-quinolin-2-one (213389-48-1) → 4-(3-chloro-phenyl)-6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-8-methoxy-1H-quinolin-2-one (213389-54-9)

Guidance literature:

1-methyl-1H-imidazole; With n-butyllithium; triethylsilyl chloride; In tetrahydrofuran; at -70 ℃;

6-(4-chloro-benzoyl)-4-(3-chloro-phenyl)-8-methoxy-1H-quinolin-2-one; With n-butyllithium; In tetrahydrofuran; at -70 ℃;

DOI:10.1016/S0960-894X(03)00180-X

Reference yield:

2-Nitroanisole (91-23-6) → 4-(3-chloro-phenyl)-6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-8-methoxy-1H-quinolin-2-one (213389-54-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: AlCl₃ / CH₂Cl₂

2.1: K₂CO₃ / acetonitrile

3.1: APTS / toluene

4.1: 27 percent / NaOH / methanol

5.1: 84 percent / H₂; aq. HCl / Pt/C / tetrahydrofuran

6.1: toluene

7.1: tBuOK / 1,2-dimethoxy-ethane

8.1: n-BuLi; ClSiEt₃ / tetrahydrofuran / -70 °C

8.2: 88 percent / n-BuLi / tetrahydrofuran / -70 °C

With hydrogenchloride; sodium hydroxide; n-butyllithium; aluminium trichloride; triethylsilyl chloride; potassium tert-butylate; hydrogen; potassium carbonate; 8-aminopyrene-1,3,6-trisulfonic acid, trisodium salt; platinum on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; toluene; acetonitrile; 1.1: Friedel-Crafts reaction;

DOI:10.1016/S0960-894X(03)00180-X

Reference yield:

3-chloro-benzonitrile (766-84-7) → 4-(3-chloro-phenyl)-6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-8-methoxy-1H-quinolin-2-one (213389-54-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 27 percent / NaOH / methanol

2.1: 84 percent / H₂; aq. HCl / Pt/C / tetrahydrofuran

3.1: toluene

4.1: tBuOK / 1,2-dimethoxy-ethane

5.1: n-BuLi; ClSiEt₃ / tetrahydrofuran / -70 °C

5.2: 88 percent / n-BuLi / tetrahydrofuran / -70 °C

With hydrogenchloride; sodium hydroxide; n-butyllithium; triethylsilyl chloride; potassium tert-butylate; hydrogen; platinum on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; toluene;

DOI:10.1016/S0960-894X(03)00180-X

upstream raw materials:

1-methyl-1H-imidazole

6-(4-chloro-benzoyl)-4-(3-chloro-phenyl)-8-methoxy-1H-quinolin-2-one

2-Nitroanisole

3-chloro-benzonitrile

Downstream raw materials:

4-(3-chloro-phenyl)-6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-8-hydroxy-1H-quinolin-2-one

6-(3-chloro-phenyl)-8-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-2,3-dihydro-1-oxa-3a-aza-phenalen-4-one

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