Ethyl bromoacetate → ethyl 2-(6-bromo-2-oxoquinolin-1(2H)-yl)acetate

HRID 2098052

Reaktionsgleichung

Reaktionsgleichung von HRID 2098052
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2.Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:7](=[O:12])[CH:6]=[CH:5]2

Komponenten

3

Edukt 2

HCID 7748Ethyl bromoacetateHCID 123789436-Bromoquinolin-2(1H)-one

Produkt 1

HCID 68786198ethyl 2-(6-bromo-2-oxoquinolin-1(2H)-yl)acetateAusbeute 100 %

Versuchsvorschrift

6-Bromoquinolin-2(1H)-one (5.03 g, 22.5 mmol) was subjected to protocol K with ethyl bromoacetate instead of methyl bromoacetate to afford 6.96 g (100% yield) of ethyl 2-(6-bromo-2-oxoquinolin-1(2H)-yl)acetate as a white solid. Method [7] Retention time 4.79 min by HPLC (M+=310 and 312) and (M+Na=332 and 334). The acetate (318 mg, 1.03 mmol) was subjected to the protocol in Example 1.53.4 to afford 228 mg (83% yield) of 2-(6-bromo-2-oxoquinolin-1(2H)-yl)acetic acid as a white solid. Method [8] Retention time 4.79 min by HPLC (M+=282 and 282) and (M+Na=304 and 306).

Quellen und Nachweise

ORD-Eintrag
ord-580a31afdd1b4a859c5152d533ee8bed
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450363B2

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