5-bromo-6-chloro-N-[(methoxycarbonyl)methyl]anthranilic acid methyl ester

Base Information

• Chemical Name: 5-bromo-6-chloro-N-[(methoxycarbonyl)methyl]anthranilic acid methyl ester
• CAS No.: 6388-45-0
• Molecular Formula: C₁₁H₁₁BrClNO₄
• Molecular Weight: 336.57

Synonyms:5-bromo-6-chloro-N-[(methoxycarbonyl)methyl]anthranilic acid methyl ester

Chemical Property of 5-bromo-6-chloro-N-[(methoxycarbonyl)methyl]anthranilic acid methyl ester

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Technology Process of 5-bromo-6-chloro-N-[(methoxycarbonyl)methyl]anthranilic acid methyl ester

There total 6 articles about 5-bromo-6-chloro-N-[(methoxycarbonyl)methyl]anthranilic acid methyl 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: 93.0%

methanol (67-56-1) + 5-bromo-6-chloro-N-[(methoxycarbonyl)methyl]-isatoic anhydride (1607828-47-6) → 5-bromo-6-chloro-N-[(methoxycarbonyl)methyl]anthranilic acid methyl ester (6388-45-0)

Guidance literature:

With sodium methylate; at 40 - 45 ℃; for 2h; Inert atmosphere;

DOI:10.1002/ejoc.201301198

Reference yield:

N-acetyl-5-bromo-6-chloroanthranilic acid (125328-77-0) → 5-bromo-6-chloro-N-[(methoxycarbonyl)methyl]anthranilic acid methyl ester (6388-45-0)

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 methylate / 2 h / 40 - 45 °C / Inert atmosphere

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

DOI:10.1002/ejoc.201301198

Reference yield:

2-amino-5-bromo-6-chlorobenzoic acid (3030-19-1) → 5-bromo-6-chloro-N-[(methoxycarbonyl)methyl]anthranilic acid methyl ester (6388-45-0)

Guidance literature:

Multi-step reaction with 3 steps

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

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

2.2: Inert atmosphere

3.1: sodium methylate / 2 h / 40 - 45 °C / Inert atmosphere

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

DOI:10.1002/ejoc.201301198

upstream raw materials:

N-acetyl-5-bromo-6-chloroanthranilic acid

2-amino-5-bromo-6-chlorobenzoic acid

5-bromo-6-chloro-isatoic anhydride

methanol

Downstream raw materials:

(5-bromo-4-chloroindol-3-yl) (β-D-galactopyranosyl)-(1→4)-β-D-glucopyranoside

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