Ethyl bromoacetate → ethyl 2-(6-nitro-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetate

HRID 2381682노트

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HRID 2381682 반응식
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]2)([O-:3])=[O:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>CN(C=O)C.O.CCOC(C)=O>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:9](=[O:14])[CH2:8][CH2:7]2)([O-:3])=[O:2]

참가 물질

7

반응물 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 51117496-Nitro-3,4-dihydroquinolin-2(1H)-one

생성물 1

HCID 43446515ethyl 2-(6-nitro-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetate

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
65 °C

실험 절차

To a mixture of 6-nitro-3,4-dihydroquinolin-2(1H)-one (0.5 g, 2.6 mmol) and Cs2CO3 (1.70 g, 5.2 mmol) in DMF (5 mL) was added ethyl 2-bromoacetate (0.317 mL, 2.86 mmol). After stirring at 65° C. for 3 h, the mixture was diluted with H2O and EtOAc, organic layer was separated, and the aqueous layer was further extracted with EtOAc, organic layers were combined, dried over Na2SO4, and was concentrated in vacuo to provide ethyl 2-(6-nitro-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetate, which was used directly for next step.

후처리

  1. customwas separated
  2. extractionthe aqueous layer was further extracted with EtOAc, organic layers
  3. dry with materialdried over Na2SO4
  4. concentrationwas concentrated in vacuo

출처 및 근거

ORD 기록
ord-d9a304369d8c4b1b91b52cbd25faa23c
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258144B2

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