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

HRID 2364942Notes

Reaction equation

HRID 2364942 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 D2 (2.0 g, 11.96 mmol) in DMF (30 ml). The mixture was stirred overnight at r.t. and was then concentrated in vacuo. The crude product was purified by column chromatography (silica gel; 0-5% MeOH/DCM as eluent) to yield intermediate D3 (2.0 g, 83%).

Workup

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

Sources & evidence

ORD record
ord-08a2d1aec01d453b9c46bd1e484debd9
Source dataset
uspto-grants-2014_04
Patent number
US08697689B2

Reaction notes

Loading…