Hydrochloric Acid → 6-(4-cyanophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one

HRID 2290273Notes

Reaction equation

HRID 2290273 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]([CH3:19])[NH:14][C:15](=[O:18])[NH:16][N:17]=2)=[CH:8][CH:7]=1.Cl.C(=O)([O-])[O-].[Na+].[Na+].[C-:27]#[N:28].[K+]>O>[C:27]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]([CH3:19])[NH:14][C:15](=[O:18])[NH:16][N:17]=2)=[CH:8][CH:7]=1)#[N:28]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 10340Sodium CarbonateHCID 133860336-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-oneHCID 23668193Sodium Nitrite

Product 1

HCID 133860616-(4-cyanophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-oneYield 45.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent4×

Procedure

A solution of sodium nitrite (1.14 g) in water (3 ml) was added dropwise to a solution of 6-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (3.06 g) in a mixture of water (12 ml) and conc. hydrochloric acid (4.5 ml) over a period of 30 minutes under ice cooling. The resultant diazonium solution was cautiously neutralized with a saturated solution of sodium carbonate in water and then a cold mixture of potassium cyanide (1.88 g) and cuprous cyanide (1.17 g) in water (12 ml) was added to the solution. After stirring for 1 hour, the resultant precipitates were collected by filtration, washed successively with water, 1N-sodium hydroxide solution, 1N-hydrochloric acid, water, and then dissolved in aqueous ethanol. The solution was treated with activated charcoal and then evaporated in vacuo. The residue was chromatographed on silica gel (190 g) with a mixture of chloroform and methanol (20:1) as an eluent. The eluents containing object compound were evaporated in vacuo and the residue was recrystallized from aqueous ethanol to give 6-(4-cyanophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (1.469 g).

Workup

  1. additionwas added to the solution
  2. customthe resultant precipitates
  3. filtrationwere collected by filtration
  4. washwashed successively with water, 1N-sodium hydroxide solution, 1N-hydrochloric acid, water
  5. dissolutiondissolved in aqueous ethanol
  6. additionThe solution was treated with activated charcoal
  7. customevaporated in vacuo
  8. customThe residue was chromatographed on silica gel (190 g) with a mixture of chloroform and methanol (20:1) as an eluent
  9. additionThe eluents containing object compound
  10. customwere evaporated in vacuo
  11. customthe residue was recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-9a24fdf1efb34553b392425325d68a71
Source dataset
uspto-grants-1986_10
Patent number
US04616015

Reaction notes

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