HCID 13475879, compound → 94937-83-4

HRID 1247885Notes

Reaction equation

HRID 1247885 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH2:8][CH2:9][C:10](=[O:13])[NH:11][N:12]=2)[N:4]=[C:3]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O=[Mn]=O.O1CCOCC1>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10](=[O:13])[NH:11][N:12]=2)[N:4]=[C:3]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 13475879HCID 13475879, compound

Product 1

HCID 1347588194937-83-4Yield 41.2%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A vigorously stirred mixture of 2.2 g of 4,5-dihydro-6-(1-methyl-2-phenyl-1H-imidazol-4-yl)-3(2H)-pyridazinone, Example 1, Isomer A, MnO2 (Aldrich Chemical, 12 g) and dioxane (175 ml) is heated to 70° C. for 22 hours. The temperature is raised to 100° C. and maintained there for another 25 hours. Additional MnO2 (8 g) is added and refluxing continued for an additional 20 hours. The mixture is filtered, washed with hot dioxane, and finally with warm tetrahydrofuran. The combined filtrate and washings are concentrated to a small volume to yield 0.9 g of 6-(1-methyl-2-phenyl-1H-imidazol-4-yl)-3(2H)-pyridazinone, as off-white crystals, mp 291°-292° C., dec.

Workup

  1. temperatureThe temperature is raised to 100° C.
  2. temperaturemaintained there for another 25 hours
  3. temperaturerefluxing
  4. filtrationThe mixture is filtered
  5. washwashed with hot dioxane
  6. concentrationThe combined filtrate and washings are concentrated to a small volume

Sources & evidence

ORD record
ord-f759820df8494172b76f156b9c0a7857
Source dataset
uspto-grants-1985_06
Patent number
US04521416

Reaction notes

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