5-bromo-4-chloro-N-[(allyloxycarbonyl)methyl]anthranilic acid allyl ester

Base Information

• Chemical Name: 5-bromo-4-chloro-N-[(allyloxycarbonyl)methyl]anthranilic acid allyl ester
• CAS No.: 1607828-49-8
• Molecular Formula: C₁₅H₁₅BrClNO₄
• Molecular Weight: 388.645

Synonyms:5-bromo-4-chloro-N-[(allyloxycarbonyl)methyl]anthranilic acid allyl ester

Chemical Property of 5-bromo-4-chloro-N-[(allyloxycarbonyl)methyl]anthranilic acid allyl ester

Chemical Property:

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Technology Process of 5-bromo-4-chloro-N-[(allyloxycarbonyl)methyl]anthranilic acid allyl ester

There total 6 articles about 5-bromo-4-chloro-N-[(allyloxycarbonyl)methyl]anthranilic acid allyl ester 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: 84.0%

5-bromo-4-chloro-N-[(allyloxycarbonyl)methyl]isatoic anhydride (1607828-46-5) + allyl alcohol (107-18-6) → 5-bromo-4-chloro-N-[(allyloxycarbonyl)methyl]anthranilic acid allyl ester (1607828-49-8)

Guidance literature:

With sodium hydride; at 20 ℃; for 6.5h; Inert atmosphere;

DOI:10.1002/ejoc.201301198

Reference yield:

N-(5-chloro-2-methylphenyl)acetamide (5900-55-0) → 5-bromo-4-chloro-N-[(allyloxycarbonyl)methyl]anthranilic acid allyl ester (1607828-49-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: bromine / acetic acid / 5 h / 20 °C / Cooling with ice

2.1: potassium permanganate; magnesium sulfate / water / 5.5 h / Reflux

3.1: sodium hydroxide; water / 4 h / Reflux

4.1: pyridine / dichloromethane; acetonitrile / 3.5 h / 45 °C / Inert atmosphere

5.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / Inert atmosphere; Cooling with ice

5.2: Inert atmosphere

6.1: sodium hydride / 6.5 h / 20 °C / Inert atmosphere

With pyridine; potassium permanganate; water; bromine; sodium hydride; magnesium sulfate; sodium hydroxide; In dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/ejoc.201301198

Reference yield:

N-acetyl-5-bromo-4-chloroanthranilic acid (1607828-44-3) → 5-bromo-4-chloro-N-[(allyloxycarbonyl)methyl]anthranilic acid allyl ester (1607828-49-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydroxide; water / 4 h / Reflux

2.1: pyridine / dichloromethane; acetonitrile / 3.5 h / 45 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / Inert atmosphere; Cooling with ice

3.2: Inert atmosphere

4.1: sodium hydride / 6.5 h / 20 °C / Inert atmosphere

With pyridine; water; sodium hydride; sodium hydroxide; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/ejoc.201301198

upstream raw materials:

N-(4-bromo-5-chloro-2-methylphenyl)-acetamide

N-(5-chloro-2-methylphenyl)acetamide

N-acetyl-5-bromo-4-chloroanthranilic acid

2-amino-5-bromo-4-chlorobenzene carboxylic acid

Downstream raw materials:

(5-bromo-6-chloroindol-3-yl)-β-D-galactopyranoside

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