Potassium Hydroxide → N-Methyl-3-(3-Methyl[1,2,4]Triazolo[4,3-B]Pyridazin-6-Yl)Aniline

HRID 329635Notes

Reaction equation

HRID 329635 reaction equation
[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:18]([CH3:21])=[N:19][N:20]=3)[N:17]=2)[CH:7]=1)C(=O)C.[OH-].[K+]>C(O)C>[CH3:1][NH:2][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:18]([CH3:21])=[N:19][N:20]=3)[N:17]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 2737312CL-285032

Product 1

HCID 2779723N-Methyl-3-(3-Methyl[1,2,4]Triazolo[4,3-B]Pyridazin-6-Yl)Aniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 13.5 g of -N-methyl-N-[3-(3-methyl-1,2,4-triazolo[4,3-b]-pyridazin-6-yl)phenyl]acetamide and 10 g of potassium hydroxide in 500 ml of ethanol was heated to reflux for 12 hours. The solution was concentrated in vacuo and the residue partitioned between 200 ml of brine and 300 ml dichloromethane. The aqueous layer was extracted with 150 ml portions of dichloromethane. The combined organic layer and extracts were dried, concentrated in vacuo and the residue recrystalized from dichloromethanehexane, to give 11.66 g of yellow crystals, mp 223°-226° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 hours
  3. concentrationThe solution was concentrated in vacuo
  4. customthe residue partitioned between 200 ml of brine and 300 ml dichloromethane
  5. extractionThe aqueous layer was extracted with 150 ml portions of dichloromethane
  6. customThe combined organic layer and extracts were dried
  7. concentrationconcentrated in vacuo
  8. customthe residue recrystalized from dichloromethanehexane

Sources & evidence

ORD record
ord-33302cfd44a14b65a054659e506953f7
Source dataset
uspto-grants-1990_01
Patent number
US04892873

Reaction notes

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