Hydrochloric Acid → HCID 135406933, compound

HRID 498025Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH3:12])[N:5]=[C:4]2[N:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[N:14]=[C:15]([CH3:16])[C:3]=12.[I-].[Na+].Cl.[OH-:26].[Na+]>CS(C)=O.O>[CH3:16][C:15]1[C:3]2[C:2](=[O:26])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][C:10]=3[CH3:12])[NH:5][C:4]=2[N:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[N:14]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 4-chloro-3,5-dimethyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline (1.65 g, 5.34 mmol), sodium iodide (0.96 g, 6.41 mmol) and conc. hydrochloric acid (1 mL) in dimethylsulfoxide (20 mL) was heated and stirred at 100° C. for 2 hours. The solution was allowed to cool to room temperature, and the residue was poured into water. The solution was made basic by the addition of an aqueous sodium hydroxide solution, and the organic matter was extracted with 10% methanol/chloroform. The extract was washed with saturated brine and water and dried over anhydrous magnesium sulfate, and the solvents were evaporated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (ethyl acetate:hexane=90:10) to give the title compound (1.13 g, 73% yield).

Workup

temperatureto cool to room temperature
extractionthe organic matter was extracted with 10% methanol/chloroform
washThe extract was washed with saturated brine and water
dry with materialdried over anhydrous magnesium sulfate
customthe solvents were evaporated under reduced pressure
customThe residue thus obtained
customwas purified by silica gel column chromatography (ethyl acetate:hexane=90:10)

Sources & evidence

ORD record: ord-6d5b26f441994e4d805e18d2d5bfee98
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949648B2

Reaction notes

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