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

HRID 404697Notes

Reaction equation

HRID 404697 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].C1(CN2C=CC(O)=CC2=O)CC1>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

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 594970761-butyl-4-hydroxy-1H-pyridine-2-oneHCID 594970981-(Cyclopropylmethyl)-4-hydroxypyridin-2(1H)-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 1-butyl-4-hydroxy-1H-pyridine-2-one (2.0 g, 11.96 mmol), which was prepared as described for description D2, in DMF (30 ml). The reaction was stirred at room temperature overnight and then it was concentrated in vacuo. The crude product was purified by column chromatography (silica gel; 0-5% methanol/DCM as eluent) to yield intermediate D3 (2.0 g, 83%).

Workup

  1. customwas prepared
  2. concentrationit was concentrated in vacuo
  3. customThe crude product was purified by column chromatography (silica gel; 0-5% methanol/DCM as eluent)

Sources & evidence

ORD record
ord-f2b90c9001be47a19a03fe57e535c90b
Source dataset
uspto-grants-2014_06
Patent number
US08748621B2

Reaction notes

Loading…