Chlorosuccinimide → 1-butyl-3-chloro-4-hydroxy-2(1H)-Pyridinone

HRID 2362805Notes

Reaction equation

HRID 2362805 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH2:9]([N:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]1=[O:20])[CH2:10][CH2:11][CH3:12]>CN(C=O)C>[CH2:9]([N:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([Cl:1])[C:14]1=[O:20])[CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 594970761-butyl-4-hydroxy-1H-pyridine-2-one

Product 1

HCID 594970741-butyl-3-chloro-4-hydroxy-2(1H)-PyridinoneYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Chlorosuccinimide (1.6 g, 11.96 mmol) was added to a solution of intermediate D5 (2.0 g, 11.96 mmol) in DMF (30 ml). The reaction mixture was stirred overnight at room temperature and was then concentrated in vacuo. The crude residue was purified by column chromatography (silica gel; 0-5% methanol/DCM as eluent) to yield intermediate D6 (2.0 g, 83%).

Workup

  1. concentrationwas then concentrated in vacuo
  2. customThe crude residue was purified by column chromatography (silica gel; 0-5% methanol/DCM as eluent)

Sources & evidence

ORD record
ord-32c1fd10ba544846ad7a947bf40dba39
Source dataset
uspto-grants-2014_04
Patent number
US08691849B2

Reaction notes

Loading…