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

HRID 889631Notes

Reaction equation

HRID 889631 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-9437f495072445d9b0ad4a886cce61a5
Source dataset
uspto-grants-2012_08
Patent number
US08252937B2

Reaction notes

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