HCID 18950547, compound → HCID 13798128, compound

HRID 1492402Notes

Reaction equation

HRID 1492402 reaction equation
[CH3:1][C:2]1[C:3]2[N:4]([CH:15]=[N:16][N:17]=2)[N:5]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]=[CH:9]2)[CH:7]=1>ClCCl.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1[C:3]2[N:4]([CH:15]=[N:16][N:17]=2)[N:5]=[C:6]([N:8]2[CH:9]=[CH:10][C:11](=[O:14])[CH2:12][CH2:13]2)[CH:7]=1

Participants

4

Reactant 1

HCID 18950547HCID 18950547, compound

Product 1

HCID 13798128HCID 13798128, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 116 mg of 1-(8-methyl-1,2,4-triazolo-[4,3-b]pyridazin-6-yl)-1,4,5,6-tetrahydro-4-pyridinol in 15 ml of dichloromethane was treated with 500 ml of manganese dioxide and heated to reflux. The mixture was refluxed for 64 hours and the solids were filtered off through Celite and washed well with fresh hot dichloromethane. Evaporation of the solvent from the filtrate gave 2,3-dihydro-1-(8-methyl-1,2,4-triazolo [4,3-b]pyridazin-6-yl)-4(1H)-pyridinone melting at about 264°-266° C. with decomposition. Crystallization of a portion of this material from methanol gave a purified product as pale yellow needles melting at about 270.5°-271.5° C. with decomposition. This material was identical with the product obtained in Example 5.

Workup

  1. temperatureheated to reflux
  2. temperatureThe mixture was refluxed for 64 hours
  3. filtrationthe solids were filtered off through Celite
  4. washwashed well with fresh hot dichloromethane
  5. customEvaporation of the solvent from the filtrate

Sources & evidence

ORD record
ord-2f1574f987c94d1385494bd3df4ed175
Source dataset
uspto-grants-1994_12
Patent number
US05374632

Reaction notes

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