Potassium Carbonate → Ethyl 2-(3-chloro-4-(quinolin-2-ylmethoxy)phenyl)acetate

HRID 446826Notes

Reaction equation

HRID 446826 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].C([O-])([O-])=O.[K+].[K+].Cl[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[O:8][CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 11031224Ethyl 3-chloro-4-hydroxyphenylacetate

Product 1

HCID 67075604Ethyl 2-(3-chloro-4-(quinolin-2-ylmethoxy)phenyl)acetateYield 46.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound ethyl 2-(3-chloro-4-hydroxyphenyl)acetate (2.0 g, 0.009 mol) in DMF (10 mL) was added K2CO3 (3.8 g, 0.02 mol) at RT. The reaction mixture was stirred for 10 minutes and then 2-(chloromethyl)quinoline (1.2 g, 0.19 mol) was added. The reaction mixture was refluxed for 16 h, quenched with ice water and filtered. The residue that was obtained was extracted with DCM (2×100 mL). The combined organic layers were washed with water and brine, dried over Na2SO4, and concentrated in vacuo to afford ethyl 2-(3-chloro-4-(quinolin-2-ylmethoxy)phenyl)acetate (1.5 g, 45%) as a solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. customquenched with ice water
  3. filtrationfiltered
  4. customThe residue that was obtained
  5. extractionwas extracted with DCM (2×100 mL)
  6. washThe combined organic layers were washed with water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5da4f39d9a244524b85492d7f8e73932
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Reaction notes

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