Acetone → HCID 14639183, compound

HRID 1460143Notes

Reaction equation

Cl[C:2]1[C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]2[NH:20][CH2:21][CH2:22][N:23]=2)=[CH:14][CH:13]=1.CC(C)([O-])C.[K+].CC(C)=O>O1CCCC1>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[C:2]3[N:3]=[CH:4][CH:5]=[CH:6][C:7]=3[C:8](=[O:9])[N:23]3[CH2:22][CH2:21][NH:20][C:19]=23)=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 20 °C

Procedure

Add a solution of 2-chloro-3-pyridinylcarbonyl chloride (4.4 g) in tetrahydrofuran (55 ml) to a stirred, cooled mixture of 2-(4-chlorophenyl)methylimidazoline (4.9 g), potassium tert.-butoxide (2.8 g) and tetrahydrofuran (200 ml). Use a bath of ice and acetone for cooling. Keep the reaction mixture in the bath for 15 minutes, and then allow it to warm to 20° C. over another 15 minutes. To the warmed mixture, add a second portion (2.8 g) of potassium tert.-butoxide; allow the reaction mixture to stir at 20° C. overnight. Evaporate solvent, partition the residue between chloroform and water, and dry the chloroform solution Use sodium sulfate as a drying agent. Filter the dried solution, evaporate the solvent, and crystallize the residue from acetonitrile to obtain 10-(4-chlorophenyl)-2,3-dihydro-imidazo[1,2-g]-[1,6]naphthyridin-5(1H)-one, mp 260°-262° C.

Workup

temperaturecooled
temperaturefor cooling
customfor 15 minutes
customEvaporate solvent, partition the residue between chloroform and water
dry with materialdry the chloroform solution Use sodium sulfate as a drying agent
filtrationFilter the dried solution
customevaporate the solvent
customcrystallize the residue from acetonitrile

Sources & evidence

ORD record: ord-3e95b7d9a0ae4974bd28ff6c9499ec9c
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05070086

Reaction notes

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