Hydrazine hydrate (1:1) → 3-Pyridinemethanamine, 6-hydrazinyl-N-(2-methoxyethyl)-

HRID 1913175Notes

Reaction equation

HRID 1913175 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][CH2:10][CH2:11][O:12][CH3:13])=[CH:4][CH:3]=1.O.[NH2:15][NH2:16]>>[NH:15]([C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][CH2:10][CH2:11][O:12][CH3:13])=[CH:4][CH:3]=1)[NH2:16]

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59216380HCID 59216380, compound

Product 1

HCID 552817943-Pyridinemethanamine, 6-hydrazinyl-N-(2-methoxyethyl)-

Procedure

3.6 g (17.7 mmol) of N-[(6-chloropyridin-3-yl)methyl]-2-methoxyethanamine [prepared analogously to WO 2004/081007] are initially charged in 4.3 ml (4.4 g, 88.5 mmol) of hydrazine hydrate and stirred at boiling point at a bath temperature of 150° C. for 16 h. The reaction solution is cooled and concentrated, and the residue is purified by column chromatography on silica gel (mobile phase: acetonitrile/water 9:1).

Workup

  1. customtemperature of 150° C.
  2. customfor 16 h
  3. temperatureThe reaction solution is cooled
  4. concentrationconcentrated
  5. customthe residue is purified by column chromatography on silica gel (mobile phase: acetonitrile/water 9:1)

Sources & evidence

ORD record
ord-d136ad90dbad4afd84b8393ecff39703
Source dataset
uspto-grants-2013_12
Patent number
US08609698B2

Reaction notes

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