Hydrazine → 2-Hydrazinyl-5-((2-methoxyethoxy)methyl)pyridine

HRID 1925175Notes

Reaction equation

HRID 1925175 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[CH3:10][O:11][CH2:12][CH2:13][O-:14].[Na+].[NH2:16][NH2:17]>COCCO>[NH:16]([C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:14][CH2:13][CH2:12][O:11][CH3:10])=[CH:4][N:3]=1)[NH2:17]

Participants

5

Reactant 3

HCID 9321HydrazineHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 23673640Ethanol, 2-methoxy-, sodium salt (1:1)

Product 1

HCID 592331002-Hydrazinyl-5-((2-methoxyethoxy)methyl)pyridineYield 27.4%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

To a solution of 2-chloro-5-(chloromethyl)pyridine (1620 mg, 10 mmol) in 2-methoxyethanol (10 mL) was added sodium 2-methoxyethanolate (5.9 g, 12.00 mmol). The mixture was stirred at room temperature for 10 min and then at 50° C. for 2 hrs. Hydrazine (1.6 g, 50.0 mmol) was then added to the mixture and the reaction was heated at 120° C. for 1 hr. The mixture was purified by preparative LCMS to provide the title compound, 2-hydrazinyl-5-((2-methoxyethoxy)methyl)pyridine (540 mg, 27.4% yield).

Workup

  1. waitat 50° C. for 2 hrs
  2. temperaturethe reaction was heated at 120° C. for 1 hr
  3. customThe mixture was purified by preparative LCMS

Sources & evidence

ORD record
ord-2a301529f2d14fe6b3b3aef5ca7e8634
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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