Acetone → HCID 23650202, compound

HRID 2238575Notes

Reaction equation

[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([OH:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.C(O)(C)C.[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]1[C:25](=[O:42])[N:26]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:27]=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)[CH:29]=1)#[N:17].CC(C)=O>O>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7]([OH:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]1[C:25](=[O:42])[N:26]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:27]=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)[CH:29]=1)#[N:17]

Participants

Conditions

Temperature: 80 °C

Procedure

A p-toluenesulfonic acid aqueous solution (1.25 mL, containing 1.97 mmol p-toluenesulfonic acid) and isopropanol (30 mL) were added to a mixture of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one (532 mg, 1.47 mmol) and acetone (5 mL), which was then stirred at 80° C. (in an oil bath). Purified water (2.25 mL) was added to the mixture before filtration. The filtrate was again heated to 80° C. and then allowed to stand for 13 hours in an oil bath, the heating of which was stopped. This mixture was then allowed to stand at 5° C. for 5 hours, followed by collecting the precipitated solid by filtration. The obtained precipitate was dried with aeration at 60° C. for about 3 hours to provide 483 mg of the title compound as pale yellow crystals.

Workup

temperatureThe filtrate was again heated to 80° C.
temperaturethe heating of which
waitto stand at 5° C. for 5 hours
customby collecting the precipitated solid
filtrationby filtration
customThe obtained precipitate was dried with aeration at 60° C. for about 3 hours

Sources & evidence

ORD record: ord-e36f1044a00d4c52b8a6035669af4ecf
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718807B2

Reaction notes

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