Methanol → HCID 178432293, compound

HRID 2372891Notes

Reaction equation

HRID 2372891 reaction equation
C/C(/N)=C\[C:4]#[N:5].Cl[C:8]1[CH:13]=CC=CC=1.[C:14]([CH2:16][C:17]([NH:19][NH2:20])=O)#[N:15].C(O[C:25](=[O:27])[CH3:26])(=O)C.[CH3:28]O>>[C:14]([C:16]1[C:25]([OH:27])=[CH:26][C:4]2[N:19]([N:20]=[C:13]([CH3:8])[N:5]=2)[C:17]=1[CH3:28])#[N:15]

Participants

6

Reactant 5

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 7964ChlorobenzeneHCID 8820Cyanoacetic acid hydrazideHCID 53247203-Aminocrotonitrile

Product 1

HCID 178432293HCID 178432293, compound

Conditions

Temperature
115 °C

Procedure

120 g of 3-aminocrotonitrile were introduced into 250 ml of anhydrous chlorobenzene and stirred at 110 to 120° C. Then 141 g of N-acetyl-N,-cyanoacetylhydrazine were introduced a little at a time, waiting after each addition until the exothermic reaction had subsided. The reaction mixture was then boiled for 2 hours and, after addition of 125 g of acetic anhydride, refluxed for a further 2 hours. The heating was then switched off; 500 ml of methanol were added at 60° to 70° C., and the mixture was allowed to cool to room temperature. The resulting suspension was filtered with suction, and the residue was washed with methanol and dried at 80° 140 g of 6-cyano-2,5-dimethyl-7-hydroxy[1,2,4]triazolo[2,3-a]-pyridine were obtained as a colorless powder which did not melt up to 350° . The compound dissolves in dilute aqueous alkalies and, after recrystallization from N-methylpyrrolidone, showes the following analysis:

Workup

  1. waitwaiting
  2. additionafter each addition
  3. customuntil the exothermic reaction
  4. temperaturerefluxed for a further 2 hours
  5. temperatureto cool to room temperature
  6. filtrationThe resulting suspension was filtered with suction
  7. washthe residue was washed with methanol
  8. dry with materialdried at 80° 140 g of 6-cyano-2,5-dimethyl-7-hydroxy[1,2,4]triazolo[2,3-a]-pyridine
  9. customwere obtained as a colorless powder which
  10. customdid not melt up to 350°
  11. dissolutionThe compound dissolves in dilute aqueous alkalies
  12. customafter recrystallization from N-methylpyrrolidone

Sources & evidence

ORD record
ord-f3dcb2eb452e40ed9957f24b07af1ae9
Source dataset
uspto-grants-1992_03
Patent number
US05101028

Reaction notes

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