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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 910870Generated: October 26, 2026

Dimethylformamide → 4-Chloro-2-[[2-chloro-4-(methylsulfonyl)phenyl]amino]-benzenepropanoic acid

https://huagongshe.com/reaction/910870

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantSodium hydrideHCID 24758—
Reactant3-[2-[2-Chloro-4-(methylsulfonyl)phenoxy]-4-(trifluoromethyl)phenyl]propanoic acidHCID 11625977—
Reactant7-Chloro-1,2,3,4-tetrahydroquinolin-2-oneHCID 13690766—
Product4-Chloro-2-[[2-chloro-4-(methylsulfonyl)phenyl]amino]-benzenepropanoic acidHCID 11552809—

Reaction Conditions

Temperature90 °C

Reaction Steps

A solution of the product from step (ii) (0.174 g) and sodium hydride (60% wt. disp. oil, 0.039 g) in DMF (10 ml) was stirred at 50° C. for 1 hour. The product from example 3 step (vi)-(vii) (0.200 g) was added and the mixture was refluxed at 90° C. for 3 hours. The mixture was partitioned between 2M sodium hydroxide and diethyl ether. The aqueous layer was acidified with 2M hydrochloric acid, extracted with ethyl acetate and the organic layer dried and concentrated under reduced pressure to give an oil. The residue was purified using RP prep HPLC. Yield 0.061 g

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08022248B2
Source datasetuspto-grants-2011_09
ORD IDord-84c433670f8646a5be55f83af31ce6cf
Source noteuspto-grants-2011_09