Potassium Carbonate → Methyl p-(2-quinolylmethoxy)phenylacetate

HRID 37128Notes

Reaction equation

HRID 37128 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[OH:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][C:4]=1[CH2:3][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 14500224Methyl p-(2-quinolylmethoxy)phenylacetateYield 84.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 2-(chloromethyl)quinoline hydrochloride (1 g, 4.6 mmol) and methyl p-hydroxyphenylacetate (0.83 g, 5 mmol) in anhydrous dimethylformamide (20 mL), was added potassium carbonate (2.33 g) and the mixture was heated at 60° C. for 8 h. Dimethylformamide was removed, and the residue was partitioned between water and chloroform. The organic phase was dried over sodium sulfate and the solvent was removed, to afford 1.68 g of a crude product that was purified by chromatography on silica gel (ethyl acetatehexane 1:1), to give 1.2 g of the title compound (yield: 84%).

Workup

  1. customDimethylformamide was removed
  2. customthe residue was partitioned between water and chloroform
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customthe solvent was removed
  5. customto afford 1.68 g of a crude product that
  6. customwas purified by chromatography on silica gel (ethyl acetatehexane 1:1)

Sources & evidence

ORD record
ord-e428d97e82804edf81db55de74322532
Source dataset
uspto-grants-1995_05
Patent number
US05420131

Reaction notes

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