Chloroform → HCID 23369778, compound

HRID 1900860Notes

Reaction equation

[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[OH:12])[NH:5][C:4](=[O:13])[CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[CH2:21](I)[CH:22]=[CH2:23].C(Cl)(Cl)Cl>CN(C)C=O.O>[CH2:23]([O:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[C:2]([CH3:14])([CH3:1])[CH2:3][C:4](=[O:13])[NH:5]2)[CH:22]=[CH2:21]

Participants

Conditions

Temperature: 100 °C

Procedure

4,4-Dimethyl-5-hydroxy-3,4-dihydrocarbostyril (3.45 g, 18.0 mmol) was dissolved in dimethylformamide (100 ml). To the solution, potassium carbonate (2.99 g, 21.7 mmol) and allyl iodide (3.33 g, 19.9 mmol) were added, and the mixture was stirred at 100° C. for 24 hours. Subsequently, potassium carbonate (1.5 g, 10.9 mmol) and allyl iodide (1.65 g, 9.82 mmol) were added and stirring was continued for 24 hours. The reaction mixture was condensed under reduced pressure. Chloroform and water were added to the residue, and extracted. After the extract was dried and condensed, the residue was purified by silica gel column chromatography (developer=chloroform:methanol=50:1). Recrystallization from a solvent mixture of chloroform-hexane-ether yielded 2.06 g of the title compound as pale yellow needles (52.3%).

Workup

stirringstirring
waitwas continued for 24 hours
customcondensed under reduced pressure
extractionextracted
customAfter the extract was dried
customcondensed
customthe residue was purified by silica gel column chromatography (developer=chloroform:methanol=50:1)
customRecrystallization
additionfrom a solvent mixture of chloroform-hexane-ether

Sources & evidence

ORD record: ord-3ace0f60730b4faab1e4a138168032d8
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05576324

Reaction notes

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