Sodium Hydroxide → HCID 21484122, compound

HRID 1414875Notes

Reaction equation

HRID 1414875 reaction equation
Cl[C:2]1[C:3](=[O:21])[N:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:5]=[CH:6][C:7]=1[N:8]([CH3:10])[NH2:9].[OH-].[Na+]>[Pd].C(O)C>[F:20][C:17]([F:18])([F:19])[C:13]1[CH:12]=[C:11]([N:4]2[C:3](=[O:21])[CH:2]=[C:7]([N:8]([CH3:10])[NH2:9])[CH:6]=[N:5]2)[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 214841104-Chloro-5-(1-methylhydrazinyl)-2-[3-(trifluoromethyl)phenyl]-3(2H)-pyridazinone

Product 1

HCID 21484122HCID 21484122, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution consisting of 15.9 grams of 4-chloro-2-(3-trifluoromethylphenyl)-5-(1-methylhydrazino)-pyridazin-3 (2H)-one prepared as in example 2, 120 grams of ethanol and 5 grams of 50 percent sodium hydroxide in a pressure reactor, 1 gram of 5 percent Palladium on carbon is added and the mixture is hydrogenated at a pressure of about 15 pounds per square inch for one hour at room temperature. The resulting product is then filtered and washed with 30 grams of warm ethanol, after which the filtrate is concentrated under reduced 3 pressure. The resulting product is dissolved in 250 grams of chloroform and washed several times with water. The chloroform layer is concentrated under reduced pressure, and the resulting solid is crystallized from benzene to yield 2-(3-trifluoromethylphenyl)-5-(1-methylhydrazino)-pyridazin-3(2H)-one, (m.p. 125° to 127° C).

Workup

  1. filtrationThe resulting product is then filtered
  2. washwashed with 30 grams of warm ethanol
  3. concentrationafter which the filtrate is concentrated under reduced 3 pressure
  4. dissolutionThe resulting product is dissolved in 250 grams of chloroform
  5. washwashed several times with water
  6. concentrationThe chloroform layer is concentrated under reduced pressure
  7. customthe resulting solid is crystallized from benzene

Sources & evidence

ORD record
ord-358d61ed0c0c40d688c1faebd9726256
Source dataset
uspto-grants-1977_01
Patent number
US04002751

Reaction notes

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