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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 530341Generated: November 3, 2026

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

https://huagongshe.com/reaction/530341

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 at 0° C. 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). 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 then stirred for 2 h before water was added. After extraction of the reaction mixture with EtOAc, the organic layer was washed with water and brine in sequence. Then, the organic layer was dried over anhy. Na2SO4 and the solvent was removed under reduced pressure to give a crude product (0.49 g, 90% yield) as a white solid. MS: 274.0 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09353081B2
Source datasetuspto-grants-2016_05
ORD IDord-f6e132b9dd544c1089f5a6d221a3a916
Source noteuspto-grants-2016_05