Formic Acid → 3-(2-Formylhydrazino)-5-methyl-6-phenyl-1,2,4-triazine

HRID 2290347Notes

Reaction equation

HRID 2290347 reaction equation
[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.[NH:11]([C:13]1[N:14]=[N:15][C:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:17]([CH3:19])[N:18]=1)[NH2:12]>CO.[OH-].[NH4+]>[CH:1]([NH:12][NH:11][C:13]1[N:14]=[N:15][C:16]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[C:17]([CH3:19])[N:18]=1)=[O:3]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 155864093-Hydrazino-5-methyl-6-phenyl-1,2,4-triazine

Product 1

HCID 202320363-(2-Formylhydrazino)-5-methyl-6-phenyl-1,2,4-triazine

Reagents, catalysts & solvents 2

HCID 14923Ammonium HydroxideCatalystHCID 887MethanolSolvent

Procedure

Formic acid (5 ml) was added dropwise to acetic anhydride (10 ml) with stirring under ice cooling, and stirred at 50° C. for 15 minutes. To the solution was added 3-hydrazino-5-methyl-6 -phenyl-1,2,4-triazine (5g) with stirring under ice cooling, and the stirring was continued for 50 minutes under ice cooling. The reaction mixture was poured into ice water, and the resultant precipitates were collected by filtration and washed with water. The above obtained solid was dissolved in methanol (100 ml), the solution was treated with 28% ammonium hydroxide (14 drops) and evaporated to give white powder of 3-(2-formylhydrazino)-5-methyl-6-phenyl-1,2,4-triazine (4.505 g).

Workup

  1. stirringstirred at 50° C. for 15 minutes
  2. stirringwith stirring under ice cooling
  3. customthe resultant precipitates
  4. filtrationwere collected by filtration
  5. washwashed with water
  6. customThe above obtained solid
  7. customevaporated

Sources & evidence

ORD record
ord-d42d06d255334be8b94925376cf4312b
Source dataset
uspto-grants-1986_10
Patent number
US04616014

Reaction notes

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