Ammonium formate → 4-(4-Methoxy-2-methylphenyl)-3-pyridazineamine

HRID 1793080Notes

Reaction equation

HRID 1793080 reaction equation
C([O-])=O.[NH4+].Cl[C:6]1[N:11]=[N:10][C:9]([NH2:12])=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=2[CH3:21])[CH:7]=1>CO.[Pd]>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:8]2[CH:7]=[CH:6][N:11]=[N:10][C:9]=2[NH2:12])=[C:14]([CH3:21])[CH:15]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 220244746-Chloro-4-(4-methoxy-2-methylphenyl)-3-pyridazineamine

Product 1

HCID 220244894-(4-Methoxy-2-methylphenyl)-3-pyridazineamineYield 90.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd—C (hydrous product; 7.89 g) and ammonium formate (11.96 g) were added to a solution of 6-chloro-4-(4-methoxy-2-methylphenyl)-3-pyridazineamine (7.89 g) in methanol (100 mL), and the mixture was heated under reflux for 1.5 hours. The reaction mixture was filtered through Celite, and the solvent was evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate:ethanol=10:1) to give the title compound (6.16 g) as white crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. filtrationThe reaction mixture was filtered through Celite
  4. customthe solvent was evaporated
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:ethanol=10:1)

Sources & evidence

ORD record
ord-07a7055c4d7c49e6ac9330386c5fda72
Source dataset
uspto-grants-2006_07
Patent number
US07078405B2

Reaction notes

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