Chlorosuccinimide → HCID 71512054, compound

HRID 576897Notes

Reaction equation

HRID 576897 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:15]=[C:14]([NH:16][CH3:17])[CH:13]=[CH:12][N:11]=1.C([O-])(=O)C.[K+]>CC(O)=O>[Cl:9][C:10]1[CH:15]=[C:14]([NH:16][CH3:17])[C:13]([Cl:1])=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 517044Potassium AcetateHCID 534169952-Chloro-N-methylpyridin-4-amine

Product 1

HCID 71512054HCID 71512054, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

N-Chlorosuccinimide (0.623 g, 4.67 mmol) was added to 2-chloro-N-methyl-pyridin-4-amine (0.50 g, 3.89 mmol) and potassium acetate (0.763 g, 7.78 mmol) in AcOH (25 mL) and the mixture was stirred at 80° C. for 1.25 hours. The mixture was cooled and concentrated in vacuo. The concentrated mixture was diluted with water, neutralised with aqueous NaOH and extracted with EtOAc (x3). The organic extracts were evaporated onto silica gel. Gradient chromatography, eluting with 10-50% EtOAc:c-Hex, gave 2,5-dichloro-N-methylpyridin-4-amine (0.114 g, 0.699 mmol, 18% yield).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. additionThe concentrated mixture was diluted with water
  4. extractionextracted with EtOAc (x3)
  5. customThe organic extracts were evaporated onto silica gel
  6. washGradient chromatography, eluting with 10-50% EtOAc

Sources & evidence

ORD record
ord-be50ea9af3794d7da9f35b723adbb402
Source dataset
uspto-grants-2015_05
Patent number
US09040540B2

Reaction notes

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