Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1774834Generated: October 27, 2026

Water → 6-Bromo-7-chloro-1-methyl-3,4-dihydro-1H-quinolin-2-one

https://huagongshe.com/reaction/1774834

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantMethyl iodideHCID 6328—
ReactantPotassium tert-butoxideHCID 23665647—
Reactant6-Bromo-7-chloro-3,4-dihydroquinolin-2(1H)-oneHCID 70979362—
SolventDimethylformamideHCID 6228—
Product6-Bromo-7-chloro-1-methyl-3,4-dihydro-1H-quinolin-2-oneHCID 8667918590%

Reaction Conditions

Temperature0 °C

Reaction Steps

Potassium tert-butoxide (0.45 g, 4.0 mmol) was added to a solution of 6-bromo-7-chloro-3,4-dihydro-1H-quinolin-2-one (0.52 g, 2.0 mmol) in DMF (5 mL) at 0° C. Then, the reaction mixture was stirred at 0° C. for 30 min and methyl iodide (0.18 g, 1.29 mmol) was added. The resulting mixture was stirred for 2 hours before water was added. After extraction of the reaction mixture with EtOAc, the organic layer was washed with water and brine in sequence. Then, it was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure to give a crude product (0.49 g, 90%) as a white solid. MS: 274.0 (M+H+)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09260408B2
Source datasetuspto-grants-2016_02
ORD IDord-3be3bf3437ab4d629f6cf74ce3801838
Source noteuspto-grants-2016_02