Methanol → [1,2,4]triazolo[4,3-a]quinoline, 1-methyl-

HRID 1606529Notes

Reaction equation

HRID 1606529 reaction equation
[NH:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[NH2:2].[C:13]([O-])([O-])(OC)[CH3:14].CO>C1(C)C(C)=CC=CC=1>[CH3:13][C:14]1[N:4]2[C:5]3[C:10]([CH:11]=[CH:12][C:3]2=[N:1][N:2]=1)=[CH:9][CH:8]=[CH:7][CH:6]=3

Participants

5

Reactant 3

HCID 887MethanolHCID 85111Quinoline, 2-hydrazinyl-HCID 536300401-Methoxyethane-1,1-diolate

Product 1

HCID 253504[1,2,4]triazolo[4,3-a]quinoline, 1-methyl-

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To 2-hydrazinoquinoline (15.9 grams; 0.1 mole) in 70 milliliters xylene was added 13.0 grams (0.11 mole) methyl orthoacetate (13.0 grams; 0.11 mole). The stirred solution was refluxed for four hours, during which the methanol that distilled from the reaction was collected. The reaction mixture was cooled overnight, and filtered to separate the desired 1-methyl-s-triazolo(4,3-a)quinoline product. It was recrystallized from 1-butanol, yield, 9.0 grams, m.p., 166°-7°C.

Workup

  1. distillationthat distilled from the reaction
  2. customwas collected
  3. temperatureThe reaction mixture was cooled overnight
  4. filtrationfiltered
  5. customto separate the desired 1-methyl-s-triazolo(4,3-a)quinoline product
  6. customIt was recrystallized from 1-butanol
  7. customyield
  8. customm.p., 166°-7°C.

Sources & evidence

ORD record
ord-8ba0b4fb5d704872b7e97514de7d85c6
Source dataset
uspto-grants-1976_04
Patent number
US03953457

Reaction notes

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