1(2H)-Pyridinecarboxylic acid, 3,4-dihydro-4-oxo-, ethyl ester

Base Information

• Chemical Name: 1(2H)-Pyridinecarboxylic acid, 3,4-dihydro-4-oxo-, ethyl ester
• CAS No.: 57330-84-4
• Molecular Formula: C8H11NO3
• Molecular Weight: 169.17800
• DSSTox Substance ID: DTXSID60415631
• Nikkaji Number: J752.282G
• Wikidata: Q82224575
• Mol file: 57330-84-4.mol

Synonyms:57330-84-4;1(2H)-Pyridinecarboxylic acid, 3,4-dihydro-4-oxo-, ethyl ester;ethyl 4-oxo-2,3-dihydropyridine-1-carboxylate;1-(Ethoxycarbonyl)-1,2,3,4-tetrahydro-4-oxopyridine;ghl.PD_Mitscher_leg0.182;SCHEMBL10654652;DTXSID60415631;OXDNIENYXPYYNI-UHFFFAOYSA-N;KUC101230N;AKOS028111781;N-ethoxycarbonyl-2,3-dihydro-4(1H)-pyridinone;4-Oxo-3,4-dihydropyridine-1(2H)-carboxylic acid ethyl ester

Chemical Property of 1(2H)-Pyridinecarboxylic acid, 3,4-dihydro-4-oxo-, ethyl ester

Chemical Property:

• PSA: 46.61000
• LogP: 0.86930
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 169.07389321
• Heavy Atom Count: 12
• Complexity: 222

Purity/Quality:

99% ^*data from raw suppliers

1-(Ethoxycarbonyl)-1,2,3,4-tetrahydro-4-oxopyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)N1CCC(=O)C=C1
• Uses: 1-(Ethoxycarbonyl)-1,2,3,4-tetrahydro-4-oxopyridine is a useful synthetic intermediate in the synthesis of (E)-Ethyl 4-(8-chloro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11(6H)-ylidene)-3,4-dihydropyridine-1(2H)-carboxylate (E902770); an impurity of Loratadine (L469575) which is a nonsedating-type histamine H1-receptor.

Technology Process of 1(2H)-Pyridinecarboxylic acid, 3,4-dihydro-4-oxo-, ethyl ester

There total 3 articles about 1(2H)-Pyridinecarboxylic acid, 3,4-dihydro-4-oxo-, ethyl ester 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: 67.0%

4-methoxypyridine (620-08-6,1232006-56-2) + chloroformic acid ethyl ester (541-41-3) → ethyl 3,4-dihydro-4-oxo-1(2H)-pyridinecarboxylate (57330-84-4)

Guidance literature:

4-methoxypyridine; With sodium tetrahydroborate; In tetrahydrofuran; isopropyl alcohol;

chloroformic acid ethyl ester; In tetrahydrofuran; isopropyl alcohol;

With hydrogenchloride; In tetrahydrofuran; isopropyl alcohol;

DOI:10.1055/s-0036-1589109

Reference yield:

ethyl 6-bromo-1,4-dioxa-8-azaspiro<4.5>decane-8-carboxylate (127619-51-6) → ethyl 3,4-dihydro-4-oxo-1(2H)-pyridinecarboxylate (57330-84-4)

Guidance literature:

With hydrogenchloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; Yield given. Multistep reaction; 1.) DMSO, 80 deg C, 11 h; 2.) methanol, 30 min.;

DOI:10.1021/jo00302a036

Reference yield:

→ ethyl 3,4-dihydro-4-oxo-1(2H)-pyridinecarboxylate (57330-84-4)

Guidance literature:

N-Ethoxycarbonyl-4-pyridon, NaBH4, Ethyl-chlorformiat;

DOI:10.1002/hlca.19750580507

upstream raw materials:

ethyl 6-bromo-1,4-dioxa-8-azaspiro<4.5>decane-8-carboxylate

4-methoxypyridine

chloroformic acid ethyl ester

Downstream raw materials:

3,4-dihydro-4-(phenylthio)-1(2H)-pyridinecarboxylate

ethyl 5,6-dihydro-2-(2-oxocyclohexyl)-1(2H)-pyridinecarboxylate

ethyl 5,6-dihydro-2-(2-oxocyclohexyl)-1(2H)-pyridinecarboxylate 2,4-dinitrophenylhydrazone

N-ethoxycarbonyl-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinone