Iodoethane → Methyl 8-cyclopropyl-4-ethoxyquinoline-2-carboxylate

HRID 545202Notes

Reaction equation

HRID 545202 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([CH:12]3[CH2:14][CH2:13]3)[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:25](I)[CH3:26]>CN(C=O)C>[CH2:25]([O:1][C:2]1[C:11]2[C:6](=[C:7]([CH:12]3[CH2:14][CH2:13]3)[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:3]=1)[CH3:26]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178498499HCID 178498499, compound

Product 1

HCID 57440905Methyl 8-cyclopropyl-4-ethoxyquinoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1.04 g (4.28 mmol) of methyl 4-hydroxy-8-cyclopropylquinoline-2-carboxylate in 11 mL of DMF was added 1.18 g of K2CO3 and 0.68 mL of ethyl iodide successively and the mixture was stirred at 60 deg C. for 12 hr. The mixture was partitioned between AcOEt and H2O and the organic layer was washed with H2O and satd. brine, dried over anhydrous Na2SO4, and then concentrated. The residue was purified on SiO2 column chromatography (eluted with n-Hex/AcOEt=19/1) to yield methyl 4-ethoxy-8-cyclopropylquinoline-2-carboxylate as a pale yellow solid.

Workup

  1. customThe mixture was partitioned between AcOEt and H2O
  2. washthe organic layer was washed with H2O and satd
  3. dry with materialbrine, dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified on SiO2 column chromatography (eluted with n-Hex/AcOEt=19/1)

Sources & evidence

ORD record
ord-a81a5716234c426aac210f887e4c6caa
Source dataset
uspto-grants-2011_05
Patent number
US07935712B2

Reaction notes

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