(Z)-2-((8-methylfuro[3,4-b]quinolin-3(1H)-ylidene)methyl)isophthalonitrile

Base Information

• Chemical Name: (Z)-2-((8-methylfuro[3,4-b]quinolin-3(1H)-ylidene)methyl)isophthalonitrile
• CAS No.: 1315508-84-9
• Molecular Formula: C₂₁H₁₃N₃O
• Molecular Weight: 323.354
• Mol file: 1315508-84-9.mol

Synonyms:(Z)-2-((8-methylfuro[3,4-b]quinolin-3(1H)-ylidene)methyl)isophthalonitrile

Chemical Property of (Z)-2-((8-methylfuro[3,4-b]quinolin-3(1H)-ylidene)methyl)isophthalonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-2-((8-methylfuro[3,4-b]quinolin-3(1H)-ylidene)methyl)isophthalonitrile

There total 6 articles about (Z)-2-((8-methylfuro[3,4-b]quinolin-3(1H)-ylidene)methyl)isophthalonitrile 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:

(Z)-3-(2,6-dicyanophenyl)-2-(prop-2-ynyloxy)-N-m-tolylacrylamide (1315508-69-0) → (Z)-2-((8-methylfuro[3,4-b]quinolin-3(1H)-ylidene)methyl)isophthalonitrile (1315508-84-9) + (Z)-2-((6-methylfuro[3,4-b]quinolin-3(1H)-ylidene)methyl)isophthalonitrile (1315508-80-5)

Guidance literature:

With trifluoromethylsulfonic anhydride; Triphenylphosphine oxide; In dichloromethane; at 0 - 20 ℃; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2011.05.067

Reference yield:

C13H10N2O3 → (Z)-2-((8-methylfuro[3,4-b]quinolin-3(1H)-ylidene)methyl)isophthalonitrile (1315508-84-9) + (Z)-2-((6-methylfuro[3,4-b]quinolin-3(1H)-ylidene)methyl)isophthalonitrile (1315508-80-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

2.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 0 - 20 °C / Inert atmosphere

2.2: pH 4 - 5

3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0 °C / Inert atmosphere

4.1: sodium hydrogencarbonate / dichloromethane / 1 h / Inert atmosphere

5.1: trifluoromethylsulfonic anhydride; Triphenylphosphine oxide / dichloromethane / 0 - 20 °C / Inert atmosphere

With oxalyl dichloride; lithium hydroxide monohydrate; tributylphosphine; trifluoromethylsulfonic anhydride; sodium hydrogencarbonate; N,N-dimethyl-formamide; Triphenylphosphine oxide; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water; 1.1: Mitsunobu reaction;

DOI:10.1016/j.tet.2011.05.067

Reference yield:

(Z)-ethyl 3-(2,6-dicyanophenyl)-2-(prop-2-ynyloxy)acrylate (1315508-54-3) → (Z)-2-((8-methylfuro[3,4-b]quinolin-3(1H)-ylidene)methyl)isophthalonitrile (1315508-84-9) + (Z)-2-((6-methylfuro[3,4-b]quinolin-3(1H)-ylidene)methyl)isophthalonitrile (1315508-80-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 0 - 20 °C / Inert atmosphere

1.2: pH 4 - 5

2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0 °C / Inert atmosphere

3.1: sodium hydrogencarbonate / dichloromethane / 1 h / Inert atmosphere

4.1: trifluoromethylsulfonic anhydride; Triphenylphosphine oxide / dichloromethane / 0 - 20 °C / Inert atmosphere

With oxalyl dichloride; lithium hydroxide monohydrate; trifluoromethylsulfonic anhydride; sodium hydrogencarbonate; N,N-dimethyl-formamide; Triphenylphosphine oxide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/j.tet.2011.05.067

upstream raw materials:

(Z)-3-(2,6-dicyanophenyl)-2-(prop-2-ynyloxy)acrylic acid

(Z)-3-(2,6-dicyanophenyl)-2-(prop-2-ynyloxy)-N-m-tolylacrylamide

(Z)-ethyl 3-(2,6-dicyanophenyl)-2-(prop-2-ynyloxy)acrylate

2,6-dicyanotoluene