tert-butyl 2-(7-(benzyloxy)-3-cyano-6-methoxyquinolin-4-yl)-2-cyanoacetate

Base Information

• Chemical Name: tert-butyl 2-(7-(benzyloxy)-3-cyano-6-methoxyquinolin-4-yl)-2-cyanoacetate
• CAS No.: 1055969-25-9
• Molecular Formula: C₂₅H₂₃N₃O₄
• Molecular Weight: 429.475
• Mol file: 1055969-25-9.mol

Synonyms:tert-butyl 2-(7-(benzyloxy)-3-cyano-6-methoxyquinolin-4-yl)-2-cyanoacetate

Chemical Property of tert-butyl 2-(7-(benzyloxy)-3-cyano-6-methoxyquinolin-4-yl)-2-cyanoacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 2-(7-(benzyloxy)-3-cyano-6-methoxyquinolin-4-yl)-2-cyanoacetate

There total 8 articles about tert-butyl 2-(7-(benzyloxy)-3-cyano-6-methoxyquinolin-4-yl)-2-cyanoacetate 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: 81.0%

7-benzyloxy-4-chloro-6-methoxyquinoline-3-carbonitrile (214476-99-0) + cyanoacetic acid tert-butyl ester (1116-98-9) → tert-butyl 2-(7-(benzyloxy)-3-cyano-6-methoxyquinolin-4-yl)-2-cyanoacetate (1055969-25-9)

Guidance literature:

With caesium carbonate; In dimethyl sulfoxide; at 100 ℃; for 4h;

Reference yield:

4-hydroxy-3-methoxybenzoic acid methyl ester (3943-74-6) → tert-butyl 2-(7-(benzyloxy)-3-cyano-6-methoxyquinolin-4-yl)-2-cyanoacetate (1055969-25-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: potassium carbonate / acetone / 3.5 h / 45 °C

2.1: nitric acid / acetic acid / 22 h

3.1: iron; acetic acid / methanol / 4 h / Heating / reflux

4.1: 5 h / Heating / reflux

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C

5.2: 4 h / -78 - -55 °C

5.3: -55 °C

6.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 2 h / Heating / reflux

7.1: caesium carbonate / dimethyl sulfoxide / 4 h / 100 °C

With n-butyllithium; oxalyl dichloride; nitric acid; iron; potassium carbonate; caesium carbonate; acetic acid; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; hexane; dichloromethane; acetic acid; dimethyl sulfoxide; acetone;

Reference yield:

7-benzyloxy-4-hydroxy-6-methoxyquinoline-3-carbonitrile (214476-89-8,914490-11-2) → tert-butyl 2-(7-(benzyloxy)-3-cyano-6-methoxyquinolin-4-yl)-2-cyanoacetate (1055969-25-9)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 2 h / Heating / reflux

2: caesium carbonate / dimethyl sulfoxide / 4 h / 100 °C

With oxalyl dichloride; caesium carbonate; N,N-dimethyl-formamide; In dichloromethane; dimethyl sulfoxide;

upstream raw materials:

7-benzyloxy-4-chloro-6-methoxyquinoline-3-carbonitrile

cyanoacetic acid tert-butyl ester

7-benzyloxy-4-hydroxy-6-methoxyquinoline-3-carbonitrile

4-hydroxy-3-methoxybenzoic acid methyl ester

Downstream raw materials:

8-(benzyloxy)-2-(1H-imidazol-1-yl)-9-methoxybenzo[c][2,7]naphthyridin-4-amine