Chlorosuccinimide → HCID 71512054, compound

HRID 1477361Notes

Reaction equation

HRID 1477361 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 (×3). 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 (×3)
  5. customThe organic extracts were evaporated onto silica gel
  6. washGradient chromatography, eluting with 10-50% EtOAc

Sources & evidence

ORD record
ord-55e0f15bad9b431ab6247d740f07bc02
Source dataset
uspto-grants-2016_08
Patent number
US09403797B2

Reaction notes

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