Ammonium Hydroxide → Pyridazine, 5-methyl-3-[3-(trifluoromethyl)phenyl]-

HRID 1731717Notes

Reaction equation

HRID 1731717 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:9]2[CH:10]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:13][CH:14]=2)=[CH:6][C:7]=1[CH3:8].[NH4+].[OH-]>[Pd].CO>[CH3:8][C:7]1[CH:6]=[C:5]([C:9]2[CH:10]=[C:11]([C:15]([F:17])([F:16])[F:18])[CH:12]=[CH:13][CH:14]=2)[N:4]=[N:3][CH:2]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 12449558HCID 12449558, compound

Product 1

HCID 10657542Pyridazine, 5-methyl-3-[3-(trifluoromethyl)phenyl]-Yield 78.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 3-chloro-4-methyl-6-(α,α,α-trifluoro-m-tolyl)pyridazine(7 g) is added 10% palladium on carbon catalyst (0.7 g) and 300 mL of MeOH containing 30 mL of concentrated NH4OH. The mixture is shaken with H2 until the uptake of H2 ceases. The mixture is filtered to remove catalyst and concentrated in vacuo and then diluted with CH2Cl2 /H2O. The organic phase is washed with water and dried over MgSO4 to yield a solid which, on recrystallization from Et2O, gives 4.8 g (78%) of an off-white solid with a melting point of 114°-116° C.

Workup

  1. filtrationThe mixture is filtered
  2. customto remove catalyst
  3. concentrationconcentrated in vacuo
  4. additiondiluted with CH2Cl2 /H2O
  5. washThe organic phase is washed with water
  6. dry with materialdried over MgSO4
  7. customto yield a solid which
  8. customon recrystallization from Et2O

Sources & evidence

ORD record
ord-7780728892704690a50f601a94727f4b
Source dataset
uspto-grants-1986_11
Patent number
US04623376

Reaction notes

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