Potassium Iodide → 5-(2-acetyl-phenoxy)-4-chloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one

HRID 2381325Notes

Reaction equation

[Cl:1][C:2]1[C:3](=[O:15])[N:4]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[N:5]=[CH:6][C:7]=1Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[OH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31](=[O:33])[CH3:32]>CC(C)=O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:31]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[O:24][C:7]1[CH:6]=[N:5][N:4]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[C:3](=[O:15])[C:2]=1[Cl:1])(=[O:33])[CH3:32]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 4,5-dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one (Intermediate 20, 60.0 g, 0.24 mol) in acetone (600 mL) was treated with potassium carbonate (28.4 g, 0.21 mol), tetrabutylammonium bromide (1.2 g), potassium iodide (38.4 g, 0.23 mol) and 1-(2-hydroxy-phenyl)-ethanone (38.4 g, 0.28 mol). The resulting reaction mixture was stirred at 25° C. for 120 h. After this time, the reaction was filtered. The filtrate was concentrated in vacuo. Silica gel column chromatography (1:10 ethyl acetate/petroleum ether) afforded 5-(2-acetyl-phenoxy)-4-chloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one (15 g, 18%).

Workup

customThe resulting reaction mixture
filtrationAfter this time, the reaction was filtered
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-96aa6ebc43f14c31adddd61d7d5334e9
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

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