142569-69-5

Basic information

• Product Name: Methyl [E]-2-[3-(S)-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl]benzoate
• Synonyms: [R-(E)-2-[3-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-oxopropyl]benzoicacidmethylester;METHYL [E]-2-[3-(S)-[3-[2-(7-CHLORO-2-QUINOLINYL)ETHENYL]PHENYL]-3-HYDROXYPROPYL]BENZOATE;2-[3-(S)-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl]-Benzoic acid;Methyl1-[E]-2-[3-(S)-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropy]benzoate;(S)-Methyl 2-(3-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-hydroxypropyl)benzoate;2-[3-(S)-[3-[2(7-CHLORO-2-QUIONYL)ETHENYL}PHENYL}-3-HYDROXYPROPYL]-BENZOIC ACID METHYL ESTER HYDRATE;Montelukast (3S)-Hydroxy Benzoate;(S,E)-Methyl 2-(3-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-hydroxypropyl)benzoate
• CAS NO: 142569-69-5
• Molecular Formula: C₂₈H₂₄ClNO₃
• Molecular Weight: 457.95
• EINECS: 1312995-182-4
• Product Categories: Aromatics Compounds;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Montelukast Intermediate
• Mol File: 142569-69-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: 88-90°C
• Boiling Point: 643.972 °C at 760 mmHg
• Flash Point: 343.262 °C
• Appearance: yellow solid
• Density: 1.279 g/cm³
• Vapor Pressure: 1.13E-16mmHg at 25°C
• Refractive Index: 1.668
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.11±0.20(Predicted)
• CAS DataBase Reference: Methyl [E]-2-[3-(S)-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl]benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl [E]-2-[3-(S)-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl]benzoate(142569-69-5)
• EPA Substance Registry System: Methyl [E]-2-[3-(S)-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl]benzoate(142569-69-5)

Safety Data

• Hazardous Substances Data: 142569-69-5(Hazardous Substances Data)

Usage

Description

Methyl [E]-2-[3-(S)-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl]benzoate is a complex organic compound with a chemical structure that features a benzoate group, a hydroxypropyl chain, and a chloroquinolinyl group. It is characterized by its yellow solid appearance and is known for its role as an intermediate in the synthesis of Montelukast.

Uses

1. Used in Pharmaceutical Industry:
Methyl [E]-2-[3-(S)-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl]benzoate is used as an intermediate in the synthesis of Montelukast for its role in the development of anti-inflammatory and anti-allergic medications.
2. Used in Chemical Synthesis:
Methyl [E]-2-[3-(S)-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl]benzoate is used as a key component in the synthesis of various complex organic compounds, particularly those with potential applications in the pharmaceutical and chemical industries.
Chemical Properties:
Methyl [E]-2-[3-(S)-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl]benzoate is a yellow solid, which indicates its stability and potential for use in various chemical reactions and applications. Its chemical structure, featuring a benzoate group and a chloroquinolinyl group, suggests its potential for further functionalization and use in the synthesis of more complex molecules.

InChI:InChI=1/C28H24ClNO3/c29-21-13-10-18(11-14-21)16-24-27(33-17-19-6-2-1-3-7-19)25(28(31)32)23-15-12-20-8-4-5-9-22(20)26(23)30-24/h1-3,6-7,10-15H,4-5,8-9,16-17H2,(H,31,32)

Upstream product

• 133791-17-0 2-(3-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-oxopropyl)benzoic acid methyl ester 
• 64-17-5 ethanol 
• 149968-11-6 methyl 2-(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-oxopropyl)benzoate 

Relevant articles and documents

Ir/SpiroPAP Catalyzed Asymmetric Hydrogenation of a Key Intermediate of Montelukast: Process Development and Potential Impurities Study

An efficient and robust process for the asymmetric hydrogenation of a key intermediate of Montelukast using the highly efficient and selective chiral spiro catalyst Ir/SpiroPAP is reported. The developed process was conducted at mild reaction temperature (30 °C) under a hydrogen pressure of 20 atm with low catalyst loading (S/C = 30000) and afforded the desired chiral alcohol intermediate in 99.5% ee. This process currently has been carried out at 30 kg scale. The process-related impurities (impurities I-V) were also identified, synthesized, and characterized by LC-MS and NMR techniques.

Lutidine-Based Chiral Pincer Manganese Catalysts for Enantioselective Hydrogenation of Ketones

A series of MnI complexes containing lutidine-based chiral pincer ligands with modular and tunable structures has been developed. The complex shows unprecedentedly high activities (up to 9800 TON; TON=turnover number), broad substrate scope (81 examples), good functional-group tolerance, and excellent enantioselectivities (85–98 % ee) in the hydrogenation of various ketones. These aspects are rare in earth-abundant metal catalyzed hydrogenations. The utility of the protocol have been demonstrated in the asymmetric synthesis of a variety of key intermediates for chiral drugs. Preliminary mechanistic investigations indicate that an outer-sphere mode of substrate–catalyst interactions probably dominates the catalysis.

Process for preparing montelukast and precursors thereof

The present invention provides a process for stereoselectively reducing 2-[3-[3-[2-(7-chloro-2-quinolinyl)ethenyl]-phenyl]-3-oxopropyyl]benzoic-acid methyl ester, to produce to produce methyl 2-[3-(S)-[3-[2-(7-chloro-2-quinolinyl)-ethenyl]phenyl]-3-hydroxypropyl]benzoate, and a process for producing montelukast or a salt thereof. The present invention further provides a process for purifying methyl 2-[3-(S)-[3-[2-(7-chloro-2-quinolinyl)-ethenyl]phenyl]-3-hydroxypropyl]benzoate. The reduction process of the present invention uses a chiral reagent and can produce the desired reduction product in high enantiomeric excess (ee).