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

HRID 2276315Notes

Reaction equation

HRID 2276315 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 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 D8 (2.0 g, 83%).

Workup

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

Sources & evidence

ORD record
ord-35745f7d93154ed8bc95101e812b8531
Source dataset
uspto-grants-2015_09
Patent number
US09132122B2

Reaction notes

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