diazo-[2-(7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carbonyl)-3-methoxyphenyl]acetic acid methyl ester

Base Information

• Chemical Name: diazo-[2-(7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carbonyl)-3-methoxyphenyl]acetic acid methyl ester
• CAS No.: 337380-67-3
• Molecular Formula: C₂₁H₁₉N₃O₆
• Molecular Weight: 409.398

Synonyms:diazo-[2-(7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carbonyl)-3-methoxyphenyl]acetic acid methyl ester

Chemical Property of diazo-[2-(7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carbonyl)-3-methoxyphenyl]acetic acid methyl ester

Chemical Property:

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Technology Process of diazo-[2-(7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carbonyl)-3-methoxyphenyl]acetic acid methyl ester

There total 4 articles about diazo-[2-(7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carbonyl)-3-methoxyphenyl]acetic 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: 88.0%

[2-(7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carbonyl)-3-methoxyphenyl]acetic acid methyl ester (337380-66-2) → diazo-[2-(7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carbonyl)-3-methoxyphenyl]acetic acid methyl ester (337380-67-3)

Guidance literature:

With 4-toluenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; for 72h;

DOI:10.1021/jo001684w

Reference yield:

5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline (94143-83-6) → diazo-[2-(7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carbonyl)-3-methoxyphenyl]acetic acid methyl ester (337380-67-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DMAP / CH₂Cl₂ / 0.25 h / 20 °C

1.2: CH₂Cl₂ / 18 h / Heating

2.1: 88 percent / DBU; TsN₃ / acetonitrile / 72 h / 20 °C

With dmap; 4-toluenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetonitrile;

DOI:10.1021/jo001684w

Reference yield:

6-Methoxy-2-(methoxycarbonylmethyl)benzoic acid (115706-57-5) → diazo-[2-(7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carbonyl)-3-methoxyphenyl]acetic acid methyl ester (337380-67-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: oxalyl chloride / CH₂Cl₂; dimethylformamide / 2 h / 20 °C

2.1: DMAP / CH₂Cl₂ / 0.25 h / 20 °C

2.2: CH₂Cl₂ / 18 h / Heating

3.1: 88 percent / DBU; TsN₃ / acetonitrile / 72 h / 20 °C

With dmap; 4-toluenesulfonyl azide; oxalyl dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo001684w

upstream raw materials:

[2-(7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carbonyl)-3-methoxyphenyl]acetic acid methyl ester

5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline

6-Methoxy-2-(methoxycarbonylmethyl)benzoic acid

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