Water → 2-[3-(Quinolin-2-ylmethoxy)-benzyloxy]-benzaldehyde

HRID 892180Notes

Reaction equation

HRID 892180 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.[CH:22](=[O:30])[C:23]1[C:24](=[CH:26][CH:27]=[CH:28][CH:29]=1)[OH:25].C([O-])([O-])=O.[K+].[K+].O>CC(C)=O>[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:25][C:24]1[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=1[CH:22]=[O:30]

Participants

6

Reactant 4

HCID 962WaterHCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 145017072-(3-Chloromethylphenoxymethyl)quinoline hydrochloride

Product 1

HCID 222412772-[3-(Quinolin-2-ylmethoxy)-benzyloxy]-benzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-(3-Chloromethyl-phenoxymethyl)-quinoline (371 mg, 1.3 mmol, example 49) and salicylaldehyde (133 μL, 1.25 mmol) are dissolved in acetone (10 mL). K2CO3 (525 mg, 3.75 mmol) is added and the contents are heated to reflux for 16 hrs. The reaction is cooled to r.t., poured into water (100 mL) and extracted with ethyl ether (3×50 mL). The ether layers are combined and washed with Brine (3×75 mL) and dried over MgSO4. The crude material is preadsorbed onto silica gel and purified by flash chromatography (silica, 20 to 25% ethyl acetate in hexanes) to give the title compound. MS (ion spray) 370 (M+H)+.

Workup

  1. temperaturethe contents are heated
  2. temperatureto reflux for 16 hrs
  3. extractionextracted with ethyl ether (3×50 mL)
  4. washwashed with Brine (3×75 mL)
  5. dry with materialdried over MgSO4
  6. custompurified by flash chromatography (silica, 20 to 25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-ac61e949e58740768d1dd9b8ef9f2a63
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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