Hydrazine hydrate (1:1) → 2-Hydrazinyl-3-methylpyridine

HRID 497943Notes

Reaction equation

HRID 497943 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.O.[NH2:10][NH2:11]>>[NH:10]([C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1)[NH2:11]

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2208322-Bromo-3-methylpyridine

Product 1

HCID 2508432-Hydrazinyl-3-methylpyridineYield 60.1%

Conditions

Temperature
100 °C

Procedure

The title compound was prepared according to the procedure described in U.S. Pat. No. 4,260,767 (1981). A mixture of 2-bromo-3-methylpyridine (29.0 g, 169 mmol) and hydrazine monohydrate (60 mL, 1.24 mol) was heated and stirred at 100° C. for 4 hours. The mixture was ice cooled, and the resulting crude crystals were filtered. The crystals were washed with cold water and air dried, and recrystallized from chloroform/hexane to give the title compound (12.5 g, 60% yield).

Workup

  1. customThe title compound was prepared
  2. temperaturewas heated
  3. temperaturecooled
  4. filtrationthe resulting crude crystals were filtered
  5. washThe crystals were washed with cold water and air
  6. customdried
  7. customrecrystallized from chloroform/hexane

Sources & evidence

ORD record
ord-af4f456eadba4a52a495a7bd0bf6a21c
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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