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

HRID 2218307Notes

Reaction equation

HRID 2218307 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-b0f3aad2265d4c29a4bbbf77cc43a567
Source dataset
uspto-grants-2008_08
Patent number
US07410976B2

Reaction notes

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