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HRID 394055Erstellt: 25. Oktober 2026

Potassium Carbonate → 5-Bromo-1-(2,6-dichlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone

https://huagongshe.com/reaction/394055

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktPotassium CarbonateHCID 11430—
EduktN-(2,6-Dichlorophenyl)-3-(2,6-dibromo-4-methoxyphenyl)-propionamideHCID 22647977—
KatalysatorCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
LösungsmittelPyridineHCID 1049—
Produkt5-Bromo-1-(2,6-dichlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinoneHCID 22647997—

Reaktionsbedingungen

Temperatur160 °C

Reaktionsschritte

To a suspension of 340 mg of N-(2,6-dichlorophenyl)-3-(2,6-dibromo-4-methoxyphenyl)-propionamide in 20 mL of pyridine was added CuI (137 mg) and powdered, dried K2CO3 (99 mg). The resulting mixture was heated to 160° C. in a sealed tube overnight (20 h), then concentrated. The reside was purified by flash chromatography on a Biotage 40S column, eluting with 100% CH2Cl2, to yield 5-Bromo-1-(2,6-dichlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone as a white solid. Mass spectrum (ESI) 402.0 (M+1). 1H NMR (500 MHz, CDCl3): δ 7.48 (d, J=8.0 Hz, 2H); 7.34 (t, J=8.0 Hz, 1H); 6.83 (d, J=2.5 Hz, 1H); 5.77 (d, J=2.5 Hz, 1H); 3.67 (s, 3H); 3.18 (m, 2H); 2.84 (m, 2H).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS06809199B2
Quelldatensatzuspto-grants-2004_10
ORD IDord-c46e5bb3780643329dfaed9cb4e27d29
Quellennotizuspto-grants-2004_10