Potassium Carbonate → 1-[2-(2(1H)-quinolon-8-yloxymethyl)phenyl]heptyl acetate

HRID 1084750Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:19]([O:22][CH:23]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH2:36]Br)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])(=[O:21])[CH3:20]>CN(C)C=O>[C:19]([O:22][CH:23]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH2:36][O:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[NH:3][C:2](=[O:1])[CH:11]=[CH:10]2)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])(=[O:21])[CH3:20]

Participants

Conditions

Temperature: 25 °C

Procedure

6.5 g of 2,8-dihydroxyquinoline, 5.5 g of anhydrous ground potassium carbonate are stirred in 100 ml of dimethylformamide at 25° C. for 1 hour. After addition of 13.1 g of 1-(2-bromomethylphenyl)heptyl acetate in 50 ml of dimethylformamide, the mixture is stirred at 25° C. for 20 hours. The solvent is removed in vacuo, the residue is taken up in 100 ml of water and the mixture is extracted 3 times with 50 ml of ethyl acetate each time. The organic phases are washed once with 50 ml of water each time, dried over Na2SO4 and concentrated in vacuo. The oil which remains is chromatographed over silica gel 60 with CH2Cl2 /ethyl acetate 10:1. The resulting product slowly crystallizes out.

Workup

customThe solvent is removed in vacuo
extractionthe mixture is extracted 3 times with 50 ml of ethyl acetate each time
washThe organic phases are washed once with 50 ml of water each time
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe oil which remains is chromatographed over silica gel 60 with CH2Cl2 /ethyl acetate 10:1
customThe resulting product slowly crystallizes out

Sources & evidence

ORD record: ord-32dfc3775469400cbfa1b71b184a05d1
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05006534

Reaction notes

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