Dimethylformamide → Methyl 1-methyl-2-phenyl-4-quinolone-6-carboxylate

HRID 986241Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2 grams of methyl 2-phenyl-4-quinolone-6-carboxylate (obtained in Example 1), 16 ml of methyl iodide, 2 grams of potassium carbonate and 50 ml of dimethyl formamide is stirred for four hours at 60° C. After cooling, the mixture is poured into water and extracted with ethyl acetate. From the extract ethylacetate is evaporated, the residue is purified by silica chromatography, and 1.8 grams of methyl 1-methyl-2-phenyl-4-quinolone-6-carboxylate, colorless powder, melting point 174° to 176° C., is obtained.

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
customFrom the extract ethylacetate is evaporated
customthe residue is purified by silica chromatography, and 1.8 grams of methyl 1-methyl-2-phenyl-4-quinolone-6-carboxylate, colorless powder, melting point 174° to 176° C.
customis obtained

Sources & evidence

ORD record: ord-4a8fa1e9fabc41258468240755039bd9
Source dataset: uspto-grants-1987_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04711898

Reaction notes

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