Ethyl 1H-pyrrolo[3,4-b]quinoline-2(3H)-carboxylate

Base Information

• Chemical Name: Ethyl 1H-pyrrolo[3,4-b]quinoline-2(3H)-carboxylate
• CAS No.: 26862-71-5
• Molecular Formula: C₁₄H₁₄N₂O₂
• Molecular Weight: 242.277
• NSC Number: 126740
• DSSTox Substance ID: DTXSID60298885
• Nikkaji Number: J1.103.278H
• Wikidata: Q82040981
• ChEMBL ID: CHEMBL2357945
• Mol file: 26862-71-5.mol

Synonyms:26862-71-5;MLS002919893;Ethyl 1H-pyrrolo[3,4-b]quinoline-2(3H)-carboxylate;NSC126740;CHEMBL2357945;DTXSID60298885;NSC-126740;SMR001797492

Chemical Property of Ethyl 1H-pyrrolo[3,4-b]quinoline-2(3H)-carboxylate

Chemical Property:

• Vapor Pressure: 7.13E-07mmHg at 25°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 242.105527694
• Heavy Atom Count: 18
• Complexity: 321

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)N1CC2=CC3=CC=CC=C3N=C2C1

Technology Process of Ethyl 1H-pyrrolo[3,4-b]quinoline-2(3H)-carboxylate

There total 8 articles about Ethyl 1H-pyrrolo[3,4-b]quinoline-2(3H)-carboxylate 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%

ethyl-3-oxo-1-pyrrolidinecarboxylate (14891-10-2) + o-aminobenzaldehyde (529-23-7) → ethyl 2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-2-carboxylate (26862-71-5)

Guidance literature:

DOI:10.1016/S0040-4020(99)00191-X

Reference yield: 74.0%

chloroformic acid ethyl ester (541-41-3) + 2-benzyl-2,3-dihydro-1H-pyrrolo[3,4-b]quinoline (30125-83-8) → ethyl 2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-2-carboxylate (26862-71-5)

Guidance literature:

In benzene; for 2h; Heating;

DOI:10.1081/SCC-200028560

Reference yield:

2-iodo-3-quinolinecarboxaldehyde (80231-40-9) → ethyl 2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-2-carboxylate (26862-71-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 90 percent / PTSA / benzene / 7 h / Heating

2.1: n-BuLi / diethyl ether; hexane / -70 °C

2.2: 64 percent / diethyl ether; hexane / 1 h / -70 - 20 °C

3.1: 92 percent / HCl / H₂O; diethyl ether / 1 h / 20 °C

4.1: methanol / 1 h / 20 °C

4.2: 80 percent / sodium borohydride; methanol / 1 h / 0 °C

5.1: 74 percent / benzene / 2 h / Heating

With hydrogenchloride; n-butyllithium; toluene-4-sulfonic acid; In methanol; diethyl ether; hexane; water; benzene;

DOI:10.1081/SCC-200028560

upstream raw materials:

ethyl-3-oxo-1-pyrrolidinecarboxylate

o-aminobenzaldehyde

chloroformic acid ethyl ester

2-benzyl-2,3-dihydro-1H-pyrrolo[3,4-b]quinoline

Downstream raw materials:

3-chloromethyl-4-oxo-2-(1-phenylcarbonyloxypropyl)-4,6-dihydroindolizino[1,2-b]quinoline

3-methyl-4-oxo-2-(1-phenylcarbonyloxypropyl)-4,6-dihydroindolizino[1,2-b]quinoline

8-methyl-7-propionylindolizino[1,2-b]quinoline-9(11H)-one

Refernces

• 1、 Chavan, Subhash P.,Pasupathy,Sivappa,Venkatraman. "Facile syntheses of ABC ring skeleton of camptothecin and related alkaloids". . p. 3099 - 3110. Retrieved 2007/10/03.
• 2、 Yadav,Sarkar, Sanjita,Chandrasekhar. "A convergent total synthesis of mappicine ketone: A leading antiviral compound". . p. 5449 - 5456. Retrieved 2007/10/03.