Hydrochloric Acid → 5-Methyl-3-(1-methylhydrazino)-6-phenyl-2,5-dihydro-1,2,4-triazine

HRID 2290335Notes

Reaction equation

HRID 2290335 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:14]([CH3:16])[NH2:15])[N:5]=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>C(O)C.[Pd]>[CH3:1][CH:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][NH:5][C:4]([N:14]([CH3:16])[NH2:15])=[N:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 20232021HCID 20232021, compound

Product 1

HCID 155863505-Methyl-3-(1-methylhydrazino)-6-phenyl-2,5-dihydro-1,2,4-triazine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-Methyl-3-(1-methylhydrazino)-6-phenyl-1,2,4-triazine (2.9 g) was dissolved in ethanol (50 ml) containing anhydrous hydrogen chloride and hydrogenated over 5% palladium on carbon (0.33 g) under atmospheric pressure at room temperature. After the theoretical amount of hydrogen gas was absorbed, the catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was neutralized with an aqueous solution of sodium carbonate and extracted with ethyl acetate. The extract was dried over sodium sulfate and concentrated under reduced pressure. The residual solid was recrystallized from ethanol to give colorless crystals of 5-methyl-3-(1-methylhydrazino)-6-phenyl-2,5-dihydro-1,2,4-triazine, mp 139.5°~141° C.

Workup

  1. customAfter the theoretical amount of hydrogen gas was absorbed
  2. filtrationthe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residual solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-f84ef2a2ccfe41f09c1e58de4df26576
Source dataset
uspto-grants-1986_10
Patent number
US04616014

Reaction notes

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