Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1916020Generated: October 25, 2026

Isopropanol → 2-[3-(S)-[3-(2-(7-Chloro-2-quinolinyl)(E/Z)ethenyl)phenyl]-3-hydroxypropyl]benzoic acid methyl ester

https://huagongshe.com/reaction/1916020

Reaction equation

Participants

RoleNameHCIDCharge
ReactantIsopropanolHCID 3776—
ReactantSulfuric acid magnesium salt (1:1)HCID 24083—
ReactantTriethanolamine hydrochlorideHCID 101814—
ReactantMethyl 2-(3-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-oxopropyl)benzoateHCID 53394881—
SolventTolueneHCID 1140—
Product2-[3-(S)-[3-(2-(7-Chloro-2-quinolinyl)(E/Z)ethenyl)phenyl]-3-hydroxypropyl]benzoic acid methyl esterHCID 54006303—

Reaction Steps

To a jacketed 2-L 3-neck flask under nitrogen with jacket temperature set at 51° C. via an external heat exchanger and equipped with internal thermometer and mechanical stirrer at 250 rpm was added 300 mL 100 mM pH 8.0 triethanolamine-HCl, 0.6 mL 1 M MgSO4, 3.0 g of SEQ ID NO:20 catalyst as prepared in Example 3, 0.1 g NADP-Naz, to give a pale yellow solution. After stirring for 10 minutes, 100 g 2-[3-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-ketopropyl]benzoic acid methyl ester was added portion-wise over ˜5 minutes. To the slurry was added 500 mL (390 g) of IPA and 100 mL (85 g) toluene. The progress of the reaction was monitored by achiral HPLC as described in Example 4 and 6. The procedure as described in Example 9 was used for sampling and sample prep.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08617853B2
Source datasetuspto-grants-2013_12
ORD IDord-56da261dbbc84ecfbf4cb29f047ffbf4
Source noteuspto-grants-2013_12