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

HRID 2381682ノート

反応式

HRID 2381682 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
65 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d9a304369d8c4b1b91b52cbd25faa23c
出典データセット
uspto-grants-2012_09
特許番号
US08258144B2

反応ノート

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