Potassium Carbonate → HCID 14552918, compound

HRID 2051176Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH2:23][C:22](=[O:24])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[O:25][CH3:26])[N:15]=2)=[CH:10][CH:9]=1.Cl[CH2:28][C:29]([N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1)=[O:30]>CC(=O)CC>[CH3:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:23]=[C:22]([O:24][CH2:28][C:29]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[O:30])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[O:25][CH3:26])[N:15]=2)=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 20 °C

Procedure

anhydrous potassium carbonate (2.28 g) is added to a stirred suspension of 2-(4-methylphenyl)-5-methoxy-4-quinolone (2.19 g) and 4-(2-chloroacetyl)morpholine (1.62 g) in 2-butanone (76 cc). The mixture is heated to reflux for 4 hours 20 minutes and cooled to room temperature (approximately 20° C.) and the solvent is evaporated off under reduced pressure. The residue is taken up with water and ethyl acetate and the organic phase is separated after settling has taken place, dried over magnesium sulphate and evaporated under reduced pressure. The residue obtained is chromatographed on silica gel, using a chloroform/acetone mixture (95:5 by volume). The solid collected is stirred in 40°-60° petroleum ether (50 cc). 4-{[2-(4-Methylphenyl)-5-methoxy-4-quinolyl]oxyacetyl}morpholine (2.3 g), m.p. 132° C., is thereby isolated.

Workup

temperatureThe mixture is heated
temperatureto reflux for 4 hours 20 minutes
customthe solvent is evaporated off under reduced pressure
customthe organic phase is separated after settling
dry with materialdried over magnesium sulphate
customevaporated under reduced pressure
customThe residue obtained
customis chromatographed on silica gel
customThe solid collected

Sources & evidence

ORD record: ord-8f44d0eaa346459b8d1257f57be11d3b
Source dataset: uspto-grants-1991_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05017576

Reaction notes

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