N-bromobutanimide → HCID 117690888, compound

HRID 1503218Notes

Reaction equation

HRID 1503218 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[C:5](=[O:8])[NH:6][CH:7]=1.[Br:10]N1C(=O)CCC1=O>C(O)(=O)C>[Br:10][C:7]1[NH:6][C:5](=[O:8])[C:4]([OH:9])=[CH:3][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 976292,3-Pyridinediol, 5-chloro-

Product 1

HCID 117690888HCID 117690888, compoundYield 5.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 5-chloro-3-hydroxypyridin-2(1H)-one (500 mg) was added acetic acid (20 ml), and N-bromosuccinimide (734 mg) was added at room temperature. The reaction mixture was stirred at room temperature for 5 hr. The obtained solid was collected by filtration and washed with ethyl acetate. The obtained residue was purified by reversed-phase column chromatography (methanol-0.1% aqueous formic acid solution) and solidified by dimethylformamide to give 6-bromo-5-chloro-3-hydroxypyridin-2(1H)-one (40 mg).

Workup

  1. additionwas added at room temperature
  2. filtrationThe obtained solid was collected by filtration
  3. washwashed with ethyl acetate
  4. customThe obtained residue was purified by reversed-phase column chromatography (methanol-0.1% aqueous formic acid solution)

Sources & evidence

ORD record
ord-e43d1c0f2149455a974b6ec819609ffa
Source dataset
uspto-grants-2015_12
Patent number
US09212147B2

Reaction notes

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