N-(4-fluorophenyl)-2-hydroxy-1,3-dioxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide

Base Information

• Chemical Name: N-(4-fluorophenyl)-2-hydroxy-1,3-dioxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide
• CAS No.: 1383785-53-2
• Molecular Formula: C₁₆H₁₁FN₂O₄
• Molecular Weight: 314.273
• Mol file: 1383785-53-2.mol

Synonyms:N-(4-fluorophenyl)-2-hydroxy-1,3-dioxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide

Chemical Property of N-(4-fluorophenyl)-2-hydroxy-1,3-dioxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(4-fluorophenyl)-2-hydroxy-1,3-dioxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide

There total 4 articles about N-(4-fluorophenyl)-2-hydroxy-1,3-dioxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide 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: 76.0%

N-(4-fluorophenyl)-2-benzyloxy-1,3-dioxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide (1383786-06-8) → N-(4-fluorophenyl)-2-hydroxy-1,3-dioxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide (1383785-53-2)

Guidance literature:

With boron trichloride;

Reference yield:

3-methoxy-2-[2-(methoxycarbonyl)phenyl]-3-oxopropanoic acid (70932-71-7) → N-(4-fluorophenyl)-2-hydroxy-1,3-dioxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide (1383785-53-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 4-methyl-morpholine / dichloromethane / 3.5 h / 0 - 20 °C

2.1: potassium hydroxide / methanol / 0.5 h / 20 °C

3.1: toluene / 12 h / Reflux; Dean-Stark

4.1: boron trichloride / dichloromethane / 20 °C

4.2: 0.25 h

With 4-methyl-morpholine; boron trichloride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; potassium hydroxide; In methanol; dichloromethane; toluene;

DOI:10.1021/ml400009t

Reference yield:

methyl 2-{1-[(benzyloxy)amino]-3-methoxy-1,3-dioxopropan-2-yl}benzoate (1174225-91-2) → N-(4-fluorophenyl)-2-hydroxy-1,3-dioxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide (1383785-53-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium hydroxide / methanol / 0.5 h / 20 °C

2.1: toluene / 12 h / Reflux; Dean-Stark

3.1: boron trichloride / dichloromethane / 20 °C

3.2: 0.25 h

With boron trichloride; potassium hydroxide; In methanol; dichloromethane; toluene;

DOI:10.1021/ml400009t

upstream raw materials:

N-(4-fluorophenyl)-2-benzyloxy-1,3-dioxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide

3-methoxy-2-[2-(methoxycarbonyl)phenyl]-3-oxopropanoic acid

methyl 2-{1-[(benzyloxy)amino]-3-methoxy-1,3-dioxopropan-2-yl}benzoate

methyl 2-(benzyloxy)-1,3-dioxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylate