Water → 2,4-Dimethoxy-3-carbethoxyquinoline

HRID 469944Notes

Reaction equation

HRID 469944 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[Li]CCCC.Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22].O>C1COCC1>[CH3:1][O:2][C:3]1[C:12]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:11]([O:13][CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 1424362,4-DimethoxyquinolineHCID 178418339Butyllithium

Product 1

HCID 129326352,4-Dimethoxy-3-carbethoxyquinolineYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2,4-dimethoxyquinoline (11.5 g, 60.8 mmol) in anhydrous THF was added dropwise n-BuLi (2.5 M in hexane, 48.6 mL, 122 mmol) at 0° C. After stirring for 1.5 h at 0° C., the mixture was added to a solution of ethyl chloroformate in anhydrous THF and stirred at 0° C. for additional 30 min and then at room temperature overnight. The reaction mixture was poured into water and extracted with CH2Cl2. The organic layer was dried over Na2SO4 and concentrated under vacuum. The resulting residue was purified by column chromatography (petroleum ether/EtOAc=50/1) to give ethyl 2,4-dimethoxyquinoline-3-carboxylate (9.6 g, 60%).

Workup

  1. stirringstirred at 0° C. for additional 30 min
  2. customat room temperature
  3. customovernight
  4. extractionextracted with CH2Cl2
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customThe resulting residue was purified by column chromatography (petroleum ether/EtOAc=50/1)

Sources & evidence

ORD record
ord-a43de486711344028ec3ae47374d8ff8
Source dataset
uspto-grants-2014_01
Patent number
US08629162B2

Reaction notes

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