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Methyl Salicylate → Methyl 2-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoate

HRID 892184
Notes
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Reaction equation

HRID 892184 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[O:7][CH2:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.C(=O)(O)[O-].[Na+].[C:27]([O:36][CH3:37])(=[O:35])[C:28]1[C:29](=[CH:31][CH:32]=[CH:33][CH:34]=1)[OH:30].[H-].[Na+].[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C.C(OCC)C>[N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[CH:18][C:9]=1[CH2:8][O:7][C:6]1[CH:5]=[C:4]([CH:21]=[CH:20][CH:19]=1)[CH2:3][O:30][C:29]1[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=1[C:27]([O:36][CH3:37])=[O:35]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 4133Methyl SalicylateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 145017072-(3-Chloromethylphenoxymethyl)quinoline hydrochloride

Product 1

HCID 22241562Methyl 2-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoate

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

The free base of 2-(3-chloromethyl-phenoxymethyl)-quinoline hydrochloride (540 mg, 1.7 mmol, example 49) is prepard by partioning the material between ethyl ether and sodium bicarbonate and drying the organic phase with magnesium sulfate. This material is then dissolved with methyl salicylate (260 mg, 1.7 mmol) in DMF (10 mL) at 0° C. and sodium hydride (60%, 65 mg 1.7 mmol) is added. The reaction is brought to room temperature for 15 min. and is then heated at 60° C. for 6 h. The reaction is cooled and partioned between ethyl acetate and a saturated ammonium chloride solution. The organic phase is dried over magnesium sulfate, filtered, concentrated in vacuo and purified by column chromatography (silica, 50 to 80% ether in hexanes) to provide the title compound; MS (ESI) 400 (M+H)+.

Workup

  1. dry with materialdrying the organic phase with magnesium sulfate
  2. temperatureThe reaction is cooled
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography (silica, 50 to 80% ether in hexanes)

Sources & evidence

ORD record
ord-d86e556c67334af399d111d12cb61b34
Source dataset
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07005440B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes