Anisole → 1-(4-Methoxyphenyl)-2-(4-(quinolin-2-ylmethoxy)phenyl)ethanone

HRID 1258282Notes

Reaction equation

HRID 1258282 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20](Cl)=[O:21])=[CH:15][CH:14]=1.[C:23]1([O:29][CH3:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH3:30][O:29][C:23]1[CH:28]=[CH:27][C:26]([C:20](=[O:21])[CH2:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][CH2:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=3)=[CH:14][CH:15]=2)=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 7519AnisoleHCID 59354817HCID 59354817, compound

Product 1

HCID 593548091-(4-Methoxyphenyl)-2-(4-(quinolin-2-ylmethoxy)phenyl)ethanoneYield 96.5%

Conditions

Temperature
80 °C

Procedure

To a stirred solution of PPA (2.0 g, 20 mmol) were added 2-(4-(quinolin-2-ylmethoxy)phenyl)acetyl chloride (2.0 g, 5.0 mmol) and anisole (1.0 g, 10 mmol) at RT under an inert atmosphere. The reaction mixture was then heated at 80° C. for 3 h, quenched with ice cold water and stirred for another 10 minutes. The precipitated solid was filtered, and then the solid was stirred in 10% NaOH solution for 1 h, extracted with DCM (2×50 mL). The combined organic layers were washed with water (2×10 mL) and brine, concentrated, and dried under vacuum to afford 1-(4-methoxyphenyl)-2-(4-(quinolin-2-ylmethoxy)phenyl)ethanone (1.85 g, 90%) as a solid.

Workup

  1. customquenched with ice cold water
  2. filtrationThe precipitated solid was filtered
  3. stirringthe solid was stirred in 10% NaOH solution for 1 h
  4. extractionextracted with DCM (2×50 mL)
  5. washThe combined organic layers were washed with water (2×10 mL) and brine
  6. concentrationconcentrated
  7. customdried under vacuum

Sources & evidence

ORD record
ord-ee9e9c9696164de98bc93dd21f5b6373
Source dataset
uspto-grants-2013_06
Patent number
US08466148B2

Reaction notes

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