Potassium Carbonate → HCID 22254473, compound

HRID 1839128Notes

Reaction equation

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

Participants

Conditions

Temperature: 26 °C

Procedure

A round bottom flask was charge with a stir bar, 2-(4-chloro-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl acetate (9.2 g, 30.5 mmol), methanol (200 mL) and potassium carbonate (0.4 g, 3.0 mmol). The reaction was judged complete after stirring for 5 hours at 26° C. The solution was partitioned between chloroform and brine. The organic layer was removed and the aqueous fraction extracted with chloroform (6×). The organic fractions were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to approximately 200 mL when crystallization was observed. The solution was stoppered and maintained at ambient temperature for 24 hours. The resulting fine white crystals were collected by filtration to provide 4.49 g of 2-(4-chloro-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)ethanol. MS (CI) for C13H12ClN3O m/z 262 (MH+), 218.

Workup

additionA round bottom flask was charge with a stir bar
customThe solution was partitioned between chloroform and brine
customThe organic layer was removed
extractionthe aqueous fraction extracted with chloroform (6×)
dry with materialdried with anhydrous sodium sulfate
concentrationconcentrated under reduced pressure to approximately 200 mL when crystallization
temperaturemaintained at ambient temperature for 24 hours
filtrationThe resulting fine white crystals were collected by filtration

Sources & evidence

ORD record: ord-3f950bf546444768b855ca67e089c75b
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06677348B2

Reaction notes

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