Water → 2,4-Dimethoxy-3-carbethoxyquinoline

HRID 1727473Notes

Reaction equation

HRID 1727473 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-e12d76cf68b9442a87a14828f0f654b5
Source dataset
uspto-grants-2009_02
Patent number
US07495103B2

Reaction notes

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