1-Amino-3-methylisoquinoline-4-carbonitrile

Base Information

• Chemical Name: 1-Amino-3-methylisoquinoline-4-carbonitrile
• CAS No.: 161468-33-3
• Molecular Formula: C11H9N3
• Molecular Weight: 183.21
• ChEMBL ID: CHEMBL3793613
• DSSTox Substance ID: DTXSID70473727
• Nikkaji Number: J624.565J
• Wikidata: Q82303325
• Mol file: 161468-33-3.mol

Synonyms:1-AMINO-3-METHYLISOQUINOLINE-4-CARBONITRILE;161468-33-3;4-Isoquinolinecarbonitrile, 1-amino-3-methyl-;CHEMBL3793613;SCHEMBL12072170;DTXSID70473727;AKOS006326708;FT-0661925;J-009832

Chemical Property of 1-Amino-3-methylisoquinoline-4-carbonitrile

Chemical Property:

• Vapor Pressure: 1.44E-06mmHg at 25°C
• Melting Point: 273-274°C
• Refractive Index: 1.672
• Boiling Point: 398.7 °C at 760 mmHg
• Flash Point: 194.9 °C
• PSA: 63.43000
• Density: 1.24 g/cm³
• LogP: 1.92718
• Storage Temp.: Refrigerator
• Solubility.: DMF, DMSO
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 183.079647300
• Heavy Atom Count: 14
• Complexity: 255

Purity/Quality:

99% ^*data from raw suppliers

1-Amino-3-methylisoquinoline-4-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=CC=CC=C2C(=N1)N)C#N

Technology Process of 1-Amino-3-methylisoquinoline-4-carbonitrile

There total 4 articles about 1-Amino-3-methylisoquinoline-4-carbonitrile 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: 100.0%

N-(4-cyano-3-methyl-1H-isochromen-1-ylidene)acetamide (161468-31-1) → 1-amino-3-methylisoquinoline-4-carbonitrile (161468-33-3)

Guidance literature:

With ammonia; In 1,4-dioxane; for 1h; Heating;

DOI:10.1080/00397919508011362

Reference yield: 78.0%

3-Aminocrotononitrile (1118-61-2) + 3-aminoindazole (874-05-5) → 1-amino-3-methylisoquinoline-4-carbonitrile (161468-33-3)

Guidance literature:

With tert.-butylhydroperoxide; copper diacetate; caesium carbonate; In decane; acetonitrile; at 60 ℃; for 20h; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.orglett.9b02288

Reference yield:

(2-cyanophenyl)acetonitrile (3759-28-2) → 1-amino-3-methylisoquinoline-4-carbonitrile (161468-33-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium acetate / 2 h / Reflux

2: ammonia / 1,4-dioxane; water / 1 h / Reflux

With ammonia; sodium acetate; In 1,4-dioxane; water;

DOI:10.1016/j.bmc.2016.03.048

upstream raw materials:

N-(4-cyano-3-methyl-1H-isochromen-1-ylidene)acetamide

acetamidine hydrochloride

(2-cyanophenyl)acetonitrile

3-Aminocrotononitrile

Refernces

• 1、 Buskes, Melissa J.,Harvey, Katherine L.,Prinz, Boris,Crabb, Brendan S.,Gilson, Paul R.,Wilson, David J.D.,Abbott, Belinda M.. "Exploration of 3-methylisoquinoline-4-carbonitriles as protein kinase A inhibitors of Plasmodium falciparum". . p. 2389 - 2396. Retrieved 2016/05/09.
• 2、 Deady, Leslie W.,Loria, Paul M.,Quazi, Nurul H.. "Fused isoquinoline systems from reactions of an iminoisocoumarin with nitrogen nucleophiles". . p. 485 - 488. Retrieved 2007/10/03.