8-Hydroxyquinoline → HCID 20062671, compound

HRID 1084749Notes

Reaction equation

HRID 1084749 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.C(=O)([O-])[O-].[K+].[K+].[C:18]([O:21][CH:22]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33]Br)[CH:28]=1)[CH2:23][CH2:24][CH2:25][CH3:26])(=[O:20])[CH3:19]>CN(C)C=O>[C:18]([O:21][CH:22]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][O:1][C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][CH:8]=[CH:7]3)[CH:28]=1)[CH2:23][CH2:24][CH2:25][CH3:26])(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 20062707HCID 20062707, compound

Product 1

HCID 20062671HCID 20062671, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.45 g of 8-hydroxyquinoline and 1.38 g of ground anhydrous potassium carbonate are stirred in 20 ml of dimethylformamide at 25° C. for 2 hours. 2.99 g of 1-(3-bromomethylphenyl)pentyl acetate, dissolved in 10 ml of dimethylformamide, are then added dropwise and the reaction mixture is stirred overnight. The solvent is distilled off in vacuo, the residue is partitioned between water/ethyl acetate and the organic phase is dried over Na2SO4 and then concentrated in vacuo. The residue is chromatographed over silica gel 60 (Merck 9385) with CH2Cl2 /methanol 100:5 (Rf =0.45). An oil is obtained in a yield of 94% of theory.

Workup

  1. additionare then added dropwise
  2. distillationThe solvent is distilled off in vacuo
  3. customthe residue is partitioned between water/ethyl acetate
  4. dry with materialthe organic phase is dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed over silica gel 60 (Merck 9385) with CH2Cl2 /methanol 100:5 (Rf =0.45)
  7. customAn oil is obtained in a yield of 94% of theory

Sources & evidence

ORD record
ord-290bc588e116406bbee833da2317ea65
Source dataset
uspto-grants-1991_04
Patent number
US05006534

Reaction notes

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