Chlorosuccinimide → 2'-Acetyl-3-chloro-4-hydroxy-5'-methyl-[1,4]bipyridinyl-2-one

HRID 516982Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[C:8]([N:10]2[C:15](C)=[CH:14][C:13]([O:17]CC3C=CC(OC)=CC=3)=[CH:12][C:11]2=[O:27])[C:7]([CH3:28])=[CH:6][N:5]=1)(=[O:3])[CH3:2].[Cl:29]N1C(=O)CCC1=O>CC(O)C.ClC(Cl)C(O)=O>[C:1]([C:4]1[CH:9]=[C:8]([N:10]2[CH:15]=[CH:14][C:13]([OH:17])=[C:12]([Cl:29])[C:11]2=[O:27])[C:7]([CH3:28])=[CH:6][N:5]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2′-acetyl-4-((4-methoxybenzyl)oxy)-5′,6-dimethyl-2H-[1,4′-bipyridin]-2-one of part C (3.3 g, 8.7 mmol) in 2-propanol (100 mL) was added N-chlorosuccinimide (1.27 g, 9.6 mmol) and 10 drops of dichloroacetic acid. The slurry was heated at 60° C. for 3 h. The resulting slurry was concentrated and the residue was partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over magnesium sulfate. The solution was concentrated in vacuo. The residue was suspended into dichloromethane and the resulting white solid was collected by vacuum filtration to provide the chlorinated deprotected product (1.16 g): MS (ES) m/e 293 (M+H).

Workup

concentrationThe resulting slurry was concentrated
customthe residue was partitioned between ethyl acetate and water
washThe organic layer was washed with water and brine
dry with materialdried over magnesium sulfate
concentrationThe solution was concentrated in vacuo
filtrationthe resulting white solid was collected by vacuum filtration

Sources & evidence

ORD record: ord-a34ffea6841240c9b350955ffbd12f9f
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115089B2

Reaction notes

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