5-Chloro-2-pyridinol → HCID 20326567, compound

HRID 372747Notes

Reaction equation

CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[Cl:14][CH2:15][C:16](=[O:19])[CH2:17]I.[Cl:20][C:21]1[CH:22]=[CH:23][C:24](=[O:27])[NH:25][CH:26]=1>>[Cl:14][CH2:15][C:16](=[O:19])[CH2:17][O:27][C:24]1[CH:23]=[CH:22][C:21]([Cl:20])=[CH:26][N:25]=1

Participants

Reactant 3

HCID 778895-Chloro-2-pyridinol

HCID 234267321-Chloro-3-iodopropan-2-one

HCID 131709961Jones' reagent

Product 1

HCID 20326567HCID 20326567, compound

Procedure

A protected ketone derivative wherein R2 is a 5-chloro-2-pyridyl radical, for use as a starting material in the process of the invention, may be obtained by reacting epichlorhydrin with hydriodic acid and sodium iodide to give 1-chloro-3-iodopropan-2-ol, which is oxidised by Jones' reagent to the ketone, 1-chloro-3-iodopropan-2-one. The ketone is reacted with 5-chloropyrid-2-one to give 1-chloro-3-(5-chloropyrid-2-yloxy)propan-2-one, which is converted to the protected ketone derivative, ClCH2.CR3.CH2OR2 wherein R2 is a 5-chloro-2-pyridyl radical, which in turn is reacted with a trialkyl phosphite to give the required protected ketone starting material, (R1O)2.PO.CH2.CR3.CH2OR2.

Sources & evidence

ORD record: ord-677aed134c994e4b988f220333cf9a4c
Source dataset: uspto-grants-1978_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04092323

Reaction notes

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