Ammonium Hydroxide → 6-Chloro-4-methylpyridazin-3-amine

HRID 1943451Notes

Reaction equation

HRID 1943451 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[CH3:8].[OH-].[NH4+].ClC1N=[N:17]C(N)=CC=1C>>[Cl:9][C:5]1[N:4]=[N:3][C:2]([NH2:17])=[C:7]([CH3:8])[CH:6]=1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 879233,6-Dichloro-4-methylpyridazineHCID 123536636-Chloro-5-methylpyridazin-3-amine

Product 1

HCID 123536646-Chloro-4-methylpyridazin-3-amineYield 85%

Conditions

Temperature
100 °C

Procedure

A 20 mL microwave vial was charged with, a stir bar, 3,6-dichloro-4-methylpyridazine (4.0 g, 24.54 mmol) and 14 mL of a new, freshly opened bottle of ammonium hydroxide. The vial was quickly sealed. The solution was heated in a microwave (Personal Chemistry, Emrys Optimizer) to 100° C. for 3 h. The vial was cooled, opened, and a stream of nitrogen was used to remove excess ammonium hydroxide. Water was added, the solid was collected by filtration, washed with water and dried to provide a mixture of 6-chloro-5-methylpyridazin-3-amine and 6-chloro-4-methylpyridazin-3-amine (3 g, 20.90 mmol, 85% yield). The mixture was used without further purification.

Workup

  1. additionA 20 mL microwave vial was charged with, a stir bar
  2. customThe vial was quickly sealed
  3. temperatureThe vial was cooled
  4. customto remove excess ammonium hydroxide
  5. additionWater was added
  6. filtrationthe solid was collected by filtration
  7. washwashed with water
  8. customdried
  9. customto provide

Sources & evidence

ORD record
ord-17f349d1596a4a1d8a51fa6bcf729892
Source dataset
uspto-grants-2013_03
Patent number
US08389527B2

Reaction notes

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