2,3-Pyridinedicarboximide

Base Information

• Chemical Name: 2,3-Pyridinedicarboximide
• CAS No.: 4664-00-0
• Molecular Formula: C7H4N2O2
• Molecular Weight: 148.121
• Hs Code.: 2933990090
• European Community (EC) Number: 225-107-1
• NSC Number: 405554
• UNII: EL02DAU9PG
• DSSTox Substance ID: DTXSID40196890
• Nikkaji Number: J85.644D
• Wikidata: Q27894174
• Mol file: 4664-00-0.mol

Synonyms:2,3-PyDCA;2,3-pyridinedicarboximide

Chemical Property of 2,3-Pyridinedicarboximide

Chemical Property:

• Appearance/Colour: Light yellow solid
• Melting Point: 233-234 °C
• Refractive Index: 1.622
• Boiling Point: 268.69°C (rough estimate)
• PKA: 8.08±0.20(Predicted)
• PSA: 59.06000
• Density: 1.47 g/cm³
• LogP: 0.29400
• Storage Temp.: Refrigerator
• Solubility.: Dichloromethane, Ether, Ethyl Acetate, Methanol
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 148.027277375
• Heavy Atom Count: 11
• Complexity: 215

Purity/Quality:

97% ^*data from raw suppliers

Quinolinimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C(=O)NC2=O)N=C1
• Uses: Quinolinimide (cas# 4664-00-0) is a compound useful in organic synthesis.

Technology Process of 2,3-Pyridinedicarboximide

There total 14 articles about 2,3-Pyridinedicarboximide 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%

Pyridine-2,3-dicarboxylic anhydride (699-98-9) → 2,3-pyridinedicarboximide (4664-00-0,303983-78-0)

Guidance literature:

With acetamide; at 165 ℃; for 2.5h;

DOI:10.1016/j.tet.2010.03.100

Reference yield: 84.0%

Pyridine-2,3-dicarboxylic acid (89-00-9) → 2,3-pyridinedicarboximide (4664-00-0,303983-78-0)

Guidance literature:

With ammonium hydroxide; at 140 ℃; for 6h; Reagent/catalyst;

Reference yield: 66.0%

Pyridine-2,3-dicarboxylic anhydride (699-98-9) + Pyridine-2,3-dicarboxylic acid (89-00-9) → 2,3-pyridinedicarboximide (4664-00-0,303983-78-0)

Guidance literature:

Pyridine-2,3-dicarboxylic acid; With acetic anhydride; Reflux;

Pyridine-2,3-dicarboxylic anhydride; With acetamide; acetic anhydride;

upstream raw materials:

acetamide

Pyridine-2,3-dicarboxylic anhydride

urea

2-cyanopyridine-3-carboxylic acid

Downstream raw materials:

7H-furo[3,4-b]pyridin-5-one

pyridine-2,3-dicarboxamide

3-amino-pyridine-2-carboxylic acid

6,7-Dihydro-7-hydroxy-5H-pyrrolo<3,4-b>pyridin-5-one

Refernces

New fused heterocyclic systems derived from pyridine-2,3-dicarboximides

10.1039/C39880000623

The research aimed to synthesize new pyrido[2',3':3,4]pyrrolo fused heterocyclic systems derived from pyridine-2,3-dicarboximides. The authors utilized a widely known procedure of cyclodehydration of α-hydroxylactams, which were formed by regioselective reduction or Grignard addition to the starting pyridine-2,3-dicarboximides. Sodium borohydride and phenylmagnesium bromide were used as reducing agents to selectively reduce the imides, yielding mixtures of regioisomeric hydroxylactams. These hydroxylactams were then subjected to acid-catalyzed cyclodehydration in refluxing trifluoroacetic acid to produce the desired fused heterocyclic products.