Potassium Carbonate → Ethyl 2-hydroxy-6-methyl-4-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoate

HRID 892188Notes

Reaction equation

HRID 892188 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[C:10]([CH3:11])=[CH:9][C:8]([OH:12])=[CH:7][C:6]=1[OH:13])[CH3:2].Cl.Cl[CH2:17][C:18]1[CH:19]=[C:20]([CH:33]=[CH:34][CH:35]=1)[O:21][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.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[OH:13][C:6]1[CH:7]=[C:8]([O:12][CH2:17][C:18]2[CH:35]=[CH:34][CH:33]=[C:20]([O:21][CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)[CH:19]=2)[CH:9]=[C:10]([CH3:11])[C:5]=1[C:4]([O:3][CH2:1][CH3:2])=[O:14]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 75653Ethyl orsellinateHCID 145017072-(3-Chloromethylphenoxymethyl)quinoline hydrochloride

Product 1

HCID 22241340Ethyl 2-hydroxy-6-methyl-4-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoate

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Procedure

2,4-Dihydroxy-6-methyl-benzoic acid ethyl ester (315 mg, 1.6 mmol) is combined with 2-(3-chloromethyl-phenoxymethyl)-quinoline hydrochloride (0.51 g, 1.6 mmol, example 49), tetrabutylammonium iodide (55 mg, 0.15 mmol) and potassium carbonate (0.48 g, 3.5 mmol) in acetone (9 mL). The reaction is heated at reflux 48 h. The reaction is partitioned between ethyl acetate and saturated ammonium chloride. The organic phase is washed with brine, dried over magnesium sulfate, filtered and concentrated to yield the crude product. This material is purified by column chromatography (silica, 3% ether in dichloromethane) to the title compound; m.p. 127–128° C., MS (ESI) 444 (M+H)+.

Workup

  1. temperatureThe reaction is heated
  2. temperatureat reflux 48 h
  3. customThe reaction is partitioned between ethyl acetate and saturated ammonium chloride
  4. washThe organic phase is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-80967c531b3b4f73860cc670aab8d41e
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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