HCID 178418361, compound → HCID 21437152, compound

HRID 2397206Notes

Reaction equation

HRID 2397206 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14](=[O:15])[C-:13]([N+:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([CH2:23][CH3:24])[CH:17]=2)[C:12]([NH:25][C:26](=[O:54])[C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][C:34](=[O:53])[CH2:35][O:36][C:37]3[CH:42]=[CH:41][C:40]([C:43]([CH2:46][CH3:47])([CH3:45])[CH3:44])=[CH:39][C:38]=3[C:48]([CH2:51][CH3:52])([CH3:50])[CH3:49])[CH:28]=2)=[N:11]1.[H][H]>C(O)C.[Ni]>[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:10]1[C:14](=[O:15])[CH:13]([N:16]2[CH2:21][CH2:20][CH:19]([CH3:22])[CH:18]([CH2:23][CH3:24])[CH2:17]2)[C:12]([NH:25][C:26](=[O:54])[C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][C:34](=[O:53])[CH2:35][O:36][C:37]3[CH:42]=[CH:41][C:40]([C:43]([CH2:46][CH3:47])([CH3:45])[CH3:44])=[CH:39][C:38]=3[C:48]([CH2:51][CH3:52])([CH3:50])[CH3:49])[CH:28]=2)=[N:11]1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178437070HCID 178437070, compound2×

Product 1

HCID 21437152HCID 21437152, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

7.9 grams of 1-(2,4,6-trichlorophenyl)-3-[3-{(2,4 -di-tert-amylphenoxy)acetamido}benzamido]-4-(3-ethyl-4-methyl-1-pyridinio)-5-oxo-2-pyrazolin-4-ide (Compound 1-3; m.p.; 162° - 165° C.) was dissolved in 500 ml of ethanol, and about 10 g of Raney nickel catalyst was added thereto. Then, reaction was conducted in an autoclave at 80° C. for 20 hours with an initial hydrogen pressure of 60 atmospheres. After the reaction, the catalyst was removed, followed by distilling off the solvent. Upon crystallizing the resulting residue from acetonitrile-ethyl acetate (10:1 by volume) 4.2 g of Compound 2-3 having a melting point of 145° - 155° C. was obtained.

Workup

  1. customThen, reaction
  2. customAfter the reaction
  3. customthe catalyst was removed
  4. distillationby distilling off the solvent
  5. customUpon crystallizing the resulting residue from acetonitrile-ethyl acetate (10:1 by volume) 4.2 g of Compound 2-3 having a melting point of 145° - 155° C.
  6. customwas obtained

Sources & evidence

ORD record
ord-0ad7fe2abe5a4b9bb5e1a092d9c6e904
Source dataset
uspto-grants-1977_05
Patent number
US04021428

Reaction notes

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