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

HRID 892184Notes

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]

Participants

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

dry with materialdrying the organic phase with magnesium sulfate
temperatureThe reaction is cooled
dry with materialThe organic phase is dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
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

Loading…