ethyl 2-chloro-5-oxo-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate

Base Information

• Chemical Name: ethyl 2-chloro-5-oxo-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate
• CAS No.: 41598-57-6
• Molecular Formula: C11H10ClNO3
• Molecular Weight: 239.65
• Mol file: 41598-57-6.mol

Synonyms:ethyl 2-chloro-5-oxo-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate

Chemical Property of ethyl 2-chloro-5-oxo-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate

Chemical Property:

• Melting Point: 97 - 98 °C (methanol)
• PSA: 56.26000
• LogP: 1.65310

Purity/Quality:

99.0% ^*data from raw suppliers

Ethyl2-chloro-5-oxo-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate 97% ^*data from reagent suppliers

Safty Information:

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Technology Process of ethyl 2-chloro-5-oxo-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate

There total 8 articles about ethyl 2-chloro-5-oxo-6,7-dihydro-5H-cyclopenta[b]pyridine-6-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: 99.0%

diethyl 2-((6-chloro-3-(ethoxycarbonyl)pyridin-2-yl)methyl)-malonate (31163-14-1) → ethyl 2-chloro-5-oxo-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate (41598-57-6)

Guidance literature:

With sodium hydride; In toluene; mineral oil; at 20 ℃; for 4h; Inert atmosphere; Reflux;

DOI:10.1021/jm2012968

Reference yield:

ethyl 2-(bromomethyl)-6-chloronicotinate (31163-13-0) → ethyl 2-chloro-5-oxo-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate (41598-57-6)

Guidance literature:

Multi-step reaction with 2 steps

1: benzene; DMF

2: NaH; benzene

With sodium hydride; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja01609a072

Reference yield:

ethyl 6-chloro-2-methylnicotinate (31163-12-9) → ethyl 2-chloro-5-oxo-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate (41598-57-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 4 h / Inert atmosphere; Reflux

2.1: sodium hydride / tetrahydrofuran; mineral oil / 12.5 h / 20 °C / Inert atmosphere

2.2: 12 h / 20 °C / Inert atmosphere

3.1: sodium hydride / toluene; mineral oil / 4 h / 20 °C / Inert atmosphere; Reflux

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); sodium hydride; In tetrahydrofuran; tetrachloromethane; toluene; mineral oil;

DOI:10.1021/jm2012968

upstream raw materials:

diethyl 2-((6-chloro-3-(ethoxycarbonyl)pyridin-2-yl)methyl)-malonate

ethyl 2-(bromomethyl)-6-chloronicotinate

ethyl 6-chloro-2-methylnicotinate

(2E,4Z)-5-ethyl 1-methyl 4-(1-aminoethylidene)pent-2-enedioate

Downstream raw materials:

C₂₃H₂₁NO₂

diethyl {2-[(2',6'-dimethylbiphenyl-3-yl)methoxy]-6,7-dihydro-5H-cyclopenta[b]pyridin-5-yl}malonate

2-[(2',6'-dimethylbiphenyl-3-yl)methoxy]-6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol

{2-[(2',6'-dimethylbiphenyl-3-yl)methoxy]-6,7-dihydro-5H-cyclopenta[b]pyridin-5-yl}acetic acid

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