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

HRID 516621Notes

Reaction equation

HRID 516621 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-d1a09d08328e43e1a0428aa54f626a7a
Source dataset
uspto-grants-2015_08
Patent number
US09114138B2

Reaction notes

Loading…