Phenol → HCID 66875343, compound

HRID 2381301Notes

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+].[C:22]1([OH:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(#N)C>[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]=1[O:28][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 4,5-dichloro-2-(tetrahydropyran-2-yl)-2H-pyridazin-3-one (Intermediate 20, 2.50 g, 10.03 mmol) in acetonitrile (111 mL, 0.09M) was treated with potassium carbonate (1.38 g, 10.03 mmol) and phenol (944 mg, 10.03 mmol). The resulting reaction mixture was heated at reflux for 3 h and then was allowed to cool to 25° C. The reaction mixture was then partitioned between water (150 mL) and methylene chloride (3×100 mL). The combined organics were dried over sodium sulfate, filtered, rinsed, and concentrated in vacuo. Silica gel column chromatography (ISCO 80 g, 30% ethyl acetate/hexanes) afforded 4-chloro-5-phenoxy-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one (2.84 g, 92%) as a clear oil; ES+-HRMS m/e calcd for C15H15N2O3Cl [M+H+] 307.0844, found 307.0843.

Workup

customThe resulting reaction mixture
temperaturewas heated
temperatureat reflux for 3 h
customThe reaction mixture was then partitioned between water (150 mL) and methylene chloride (3×100 mL)
dry with materialThe combined organics were dried over sodium sulfate
filtrationfiltered
washrinsed
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-98fabfbfce2247f798d0cccd9028cfd8
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

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