N-(2,6-dichloro-3-pyridylmethyl)phthalimide → (2,6-Dichloropyridin-3-YL)methanamine

HRID 1954943Notes

Reaction equation

HRID 1954943 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][N:9]2C(=O)C3=CC=CC=C3C2=O)=[CH:6][CH:5]=[C:4]([Cl:20])[N:3]=1>CCO.CN(C=O)C>[Cl:1][C:2]1[C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=[C:4]([Cl:20])[N:3]=1

Participants

4

Reactant 1

HCID 22450439N-(2,6-dichloro-3-pyridylmethyl)phthalimide

Product 1

HCID 15477284(2,6-Dichloropyridin-3-YL)methanamineYield 81.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

In a mixture of 50 ml EtOH and 20 ml DMF was dissolved 3.1 g (0.01 mole) of N-(2,6-dichloro-3-pyridylmethyl)phthalimide under heating, followed by addition of 0.75 g (0.015 mole) of H2NNH2 ·H2O under reflux. After 1 hour of refluxing, EtOH and DMF were distilled off. To the residue were added 10 ml of concentrated hydrochloric acid and 5 ml of water, and the mixture was refluxed for 30 minutes. The resulting crystals were filtered off and the filtrate was neutralized with NaHCO3 and extracted with CH2Cl2 (30 ml×3). The extract was dried over MGSO4 and the solvent was distilled off to give 1.45 g of the title compound as a yellow oil.

Workup

  1. temperatureunder heating
  2. temperatureunder reflux
  3. temperatureAfter 1 hour of refluxing
  4. distillationEtOH and DMF were distilled off
  5. additionTo the residue were added 10 ml of concentrated hydrochloric acid and 5 ml of water
  6. temperaturethe mixture was refluxed for 30 minutes
  7. filtrationThe resulting crystals were filtered off
  8. extractionextracted with CH2Cl2 (30 ml×3)
  9. customThe extract was dried over MGSO4
  10. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-099de4b1fdd64c3a87198c48fa0c5398
Source dataset
uspto-grants-2000_09
Patent number
US06124297

Reaction notes

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