Hydrazine → HCID 12998749, compound

HRID 1606530Notes

Reaction equation

HRID 1606530 reaction equation
Cl[C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:13][NH2:14].O1CCOC[CH2:16]1>C(O)=O>[Cl:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]2[CH:16]=[N:13][N:14]=[C:2]2[CH:11]=1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 312751,4-Dioxane2×HCID 6075032,4-Dichloroquinoline

Product 1

HCID 12998749HCID 12998749, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

2,4-Dichloroquinoline (1.0 mole) was combined with 1 mole of anhydrous hydrazine in 4 liters of dioxane. The reaction mixture was heated at reflux for 12 hours at which time the reaction mixture was allowed to cool and the dioxane was stripped off. The resultant solid was refluxed for twelve hours in formic acid, then allowed to cool and the formic acid stripped off. The 5-chloro-s-triazolo(4,3-a)quinoline was then isolated and purified by column chromatography. A silica gel column was used with a 5 percent methanol/95 percent ethyl acetate solution as the eluant. The purified product melted at 242°-3.5°C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 12 hours at which time the reaction mixture
  3. temperatureto cool
  4. temperatureto cool

Sources & evidence

ORD record
ord-b75383f433ef4f5baa005f7c5dcea861
Source dataset
uspto-grants-1976_04
Patent number
US03953457

Reaction notes

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