Water → 5-(Aminomethyl)-2-chloropyridine

HRID 1682185Notes

Reaction equation

HRID 1682185 reaction equation
O.NN.[Cl:4][C:5]1[N:10]=[CH:9][C:8]([CH2:11][N:12]2C(=O)C3=CC=CC=C3C2=O)=[CH:7][CH:6]=1.O>CCO>[Cl:4][C:5]1[N:10]=[CH:9][C:8]([CH2:11][NH2:12])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 143247132-[(6-Chloropyridin-3-yl)methyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 70209275-(Aminomethyl)-2-chloropyridineYield 70.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (1.7 ml) was added to a refluxing solution of 6.5 g (2.4×10-2 mole) of N-(6-chloro-3-pyridylmethyl)phthalimide in 100 ml of EtOH, and the mixture was further refluxed for 1 hour. After addition of 20 ml of water, the ethanol was distilled off under reduced pressure. Concentrated hydrochloric acid (25 ml) was added to the residue and the mixture was refluxed for 1 hour. After cooling, the reaction mixture was neutralized with NaOH and the aqueous layer was saturated with NaCl and extracted with Et2O. The extract was dried over Na2SO4 and the solvent was distilled off to give 2.4 g of the title compound as a yellow oil.

Workup

  1. temperaturethe mixture was further refluxed for 1 hour
  2. distillationthe ethanol was distilled off under reduced pressure
  3. additionConcentrated hydrochloric acid (25 ml) was added to the residue
  4. temperaturethe mixture was refluxed for 1 hour
  5. temperatureAfter cooling
  6. extractionextracted with Et2O
  7. dry with materialThe extract was dried over Na2SO4
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-7a598a427ca74a9ab89a78c29a160c4c
Source dataset
uspto-grants-1992_12
Patent number
US05175301

Reaction notes

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