Ammonium Hydroxide → 3,5-Dichloro-1,4-dihydropyridazin-4-imine

HRID 1845998Notes

Reaction equation

HRID 1845998 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1Cl.[NH4+:10].[OH-]>CCO>[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[NH2:10]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 701113,4,5-Trichloropyridazine

Product 1

HCID 64032013,5-Dichloro-1,4-dihydropyridazin-4-imineYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3,4,5-trichloropyridazine (Preparation 3, 500 mg, 2.73 mmole) in EtOH (5.5 mL) and NH4OH (5.5 mL) was heated under microwave irradiation 120° C. for 25 minutes. Concentration under reduced pressure and purification via silica gel column chromatography eluting with acetone:dichloromethane (0-15% acetone), provided the title product in 36% yield, 163 mg.

Workup

  1. concentrationConcentration
  2. customunder reduced pressure and purification via silica gel column chromatography
  3. washeluting with acetone

Sources & evidence

ORD record
ord-684ad457d66744869237a591806839a4
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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