Hydrazine hydrate (1:1) → HCID 67454681, compound

HRID 2366074Notes

Reaction equation

HRID 2366074 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:4][N:3]=1.O.[NH2:17][NH2:18]>O>[NH:17]([C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:4][N:3]=1)[NH2:18]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86659956HCID 86659956, compound

Product 1

HCID 67454681HCID 67454681, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 0.5 g (2.27 mmol) of 2-chloro-4-(pyridin-3-ylmethoxy)pyridine and 2 mL (40.5 mmol) of hydrazine hydrate is heated at 80° C. for 12 hours. The reaction medium is then taken up in 30 mL of water and extracted with EtOAc (3×30 mL). The organic phases are combined, washed with brine (20 mL) and then dried over Na2SO4, filtered, concentrated under reduced pressure and purified on silica gel, eluting with a 95/5 DCM/MeOH mixture. 197 mg of 2-hydrazinyl-4-(pyridin-3-ylmethoxy)pyridine are obtained in the form of a yellow oil.

Workup

  1. extractionextracted with EtOAc (3×30 mL)
  2. washwashed with brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. custompurified on silica gel
  7. washeluting with a 95/5 DCM/MeOH mixture

Sources & evidence

ORD record
ord-b16a44d4d7c845a6aa15b41a02b52cd6
Source dataset
uspto-grants-2014_04
Patent number
US08697731B2

Reaction notes

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