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

HRID 2281456Notes

Reaction equation

HRID 2281456 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5a5a5d78a860402da0daa1b81535f79b
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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