Hydrochloric Acid → HCID 178437521, compound

HRID 2372893Notes

Reaction equation

HRID 2372893 reaction equation
[CH3:1]/[C:2](/[NH2:6])=[CH:3]\[C:4]#[N:5].[C:7]([NH:11]N)(=O)[CH2:8][CH3:9].Cl.[OH2:14]>C(N)=O>[C:4]([C:3]1[C:9]([OH:14])=[CH:8][C:7]2[N:6]([N:5]=[C:4]([CH2:3][CH3:2])[N:11]=2)[C:2]=1[CH3:1])#[N:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 79890PropionylhydrazineHCID 53247203-Aminocrotonitrile

Product 1

HCID 178437521HCID 178437521, compound

Reagents, catalysts & solvents 1

HCID 713FormamideSolvent

Conditions

Temperature
100 °C

Procedure

125 g of 3-aminocrotonitrile were dissolved in 500 ml of formamide and heated to 100° C. To this were added 155 g of N-cyanoacetyl-N,-propionylhydrazine in such a way that the exothermic reaction had subsided before the next addition. The mixture was then stirred at 120° to 125° C. for 6 hours and allowed to cool. It was then diluted with 1000 ml of water and acidified with concentrated hydrochloric acid. Filtration with suction, washing with water and drying at 100° C. resulted in 141 g of 6-cyano-2-ethyl-7-hydroxy-5-methyl[1,2,4]triazolo-[2,3-a]pyridine. A sample recrystallized from N-methylpyrrolidone melts at 346° to 348° C. and has the following analysis:

Workup

  1. additionTo this were added 155 g of N-cyanoacetyl-N
  2. additionhad subsided before the next addition
  3. temperatureto cool
  4. filtrationFiltration with suction
  5. washwashing with water
  6. customdrying at 100° C.
  7. customresulted in 141 g of 6-cyano-2-ethyl-7-hydroxy-5-methyl[1,2,4]triazolo-[2,3-a]pyridine
  8. customA sample recrystallized from N-methylpyrrolidone melts at 346° to 348° C.

Sources & evidence

ORD record
ord-07b1ca103bdd4b94a779000b1432b495
Source dataset
uspto-grants-1992_03
Patent number
US05101028

Reaction notes

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