Hydrazine hydrate (1:1) → 1-(6-Chloropyridin-2-yl)-2-(pyridin-2-yl)ethylamine

HRID 1736482Notes

Reaction equation

HRID 1736482 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH:8]([N:16]2C(=O)C3=CC=CC=C3C2=O)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:4][CH:3]=1.O.NN>CO>[Cl:1][C:2]1[N:7]=[C:6]([CH:8]([NH2:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19973564N-{1-(6-Chloropyridin-2-yl)-2-(pyridin-2-yl)ethyl}phthalimide

Product 1

HCID 199735601-(6-Chloropyridin-2-yl)-2-(pyridin-2-yl)ethylamineYield 45.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 l of methanol was mixed with 77 g of the crude N-{1-(6-chloropyridin-2-yl)-2-(pyridin-2-yl)ethyl}-phthalimide prepared in the Preparative Example 23 and 16.5 g of hydrazine monohydrate. The obtained mixture was heated under reflux for 2 hours to conduct a reaction. After the reaction mixture was allowed to stand at room temperature, the precipitated crystals were filtered out and the filtrate was concentrated. Water and ethyl acetate were added to the concentrate to conduct extraction. The organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (with a methanol/dichloromethane (5:95 mixture) to give 22.38 g of the title compound.

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customa reaction
  4. customto stand at room temperature
  5. filtrationthe precipitated crystals were filtered out
  6. concentrationthe filtrate was concentrated
  7. additionWater and ethyl acetate were added to the
  8. concentrationconcentrate
  9. extractionextraction
  10. washThe organic phase was washed with a saturated aqueous solution of common salt
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated
  13. customThe residue was purified by silica gel chromatography (with a methanol/dichloromethane (5:95 mixture)

Sources & evidence

ORD record
ord-bc68151492af4ca8bdbea9f1d961134c
Source dataset
uspto-grants-1996_07
Patent number
US05541213

Reaction notes

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