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

HRID 35639Notes

Reaction equation

HRID 35639 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)AnilineYield 101.5%

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 of 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 dichloromethane-hexane, to give 11.66 g of yellow crystal, 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 of 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 dichloromethane-hexane

Sources & evidence

ORD record
ord-4e025dd7c9f8466dacaac0e67d2eb0b4
Source dataset
uspto-grants-1988_08
Patent number
US04767765

Reaction notes

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