Lithium iodide → HCID 70136544, compound

HRID 1419499Notes

Reaction equation

[I-].[Li+].[Cl:3][C:4]1[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[C:5]=1[C:6]([C:8]1[CH:9]=[C:10]([C:19]([O:22]C)=[CH:20][CH:21]=1)[CH2:11][C:12]1[CH:13]=[CH:14][C:15](=[O:18])[NH:16][N:17]=1)=[O:7]>N1C(C)=CC(C)=CC=1C>[Cl:3][C:4]1[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[C:5]=1[C:6]([C:8]1[CH:9]=[C:10]([C:19]([OH:22])=[CH:20][CH:21]=1)[CH2:11][C:12]1[CH:13]=[CH:14][C:15](=[O:18])[NH:16][N:17]=1)=[O:7]

Participants

Conditions

Temperature: 165 °C

Procedure

Lithium iodide (4.0 g, 29.7 mmol) was added to a solution of 6-[3-(2,4,6-trichlorobenzoyl)-6-methoxybenzyl]-2H-pyridazin-3-one (2.5 g, 5.9 mmol) [prepared by proceeding as described in Example 3, but replacing 2-fluorophenylacetic acid with 2-methoxyphenylacetic acid] in 2,4,6-collidine (250 ml) and the reaction mixture was heated to 165° C. After 3 h the reaction mixture was cooled to room temperature, and the product was extracted into ethyl acetate. The organic extract was washed with aqueous HCl (5%), NaHCO3 and brine, and dried over MgSO4. The organic solvent was removed in vacuo to give 2.25 g of crude product, which upon recrystallization from chloroform/hexanes gave pure 6-[3-(2,4,6-trichlorobenzoyl)-6-hydroxybenzyl]-2H-pyridazin-3-one (1.97 g) as a solid, mp 257.8° C.

Workup

temperatureAfter 3 h the reaction mixture was cooled to room temperature
extractionthe product was extracted into ethyl acetate
extractionThe organic extract
washwas washed with aqueous HCl (5%), NaHCO3 and brine
dry with materialdried over MgSO4
customThe organic solvent was removed in vacuo
customto give 2.25 g of crude product, which
customupon recrystallization from chloroform/hexanes

Sources & evidence

ORD record: ord-1e522008e42b4541b746c0b2086751ba
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05886178

Reaction notes

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