L 10503 → 2-(3-Methoxyphenyl)[1,2,4]triazolo[5,1-a]isoquinoline

HRID 616695Notes

Reaction equation

HRID 616695 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:21]=[C:12]3[C:13]4[C:18]([CH2:19][CH2:20][N:11]3[N:10]=2)=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH:6]=[CH:7][CH:8]=1>[O-2].[O-2].[Mn+4].C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:21]=[C:12]3[C:13]4[C:18]([CH:19]=[CH:20][N:11]3[N:10]=2)=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 100434L 10503

Product 1

HCID 1344002-(3-Methoxyphenyl)[1,2,4]triazolo[5,1-a]isoquinolineYield 70%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 241BenzeneSolvent2×

Procedure

Thirty five grams of wet manganese dioxide, prepared as described by E. Pratt and J. Van de Castle, J. Org. Chem. 26, 2973 (1961) is suspended in 200 ml. of benzene, according to the procedure outlined by J. Goldman, J. Org. Chem. 34, 1979 (1969). The mixture is refluxed for about three hours, then a solution of 2.77 g. (0.010 mole) of 2-(m-methoxyphenyl)-5,6-dihydro-s-triazolo[5,1-a]isoquinoline in 30 ml. of anhydrous benzene is added. Refluxing is prolonged for a further six hours, then the reaction mixture is allowed to stand overnight. 20 Grams of the above manganese dioxide is added and the resulting suspension is refluxed for 8 hours. After cooling, the solid catalyst is filtered off, the benzene solution is dried under vacuum and a residue is obtained which is recrystallized from ethyl acetate. Yield 1.4 g., m.p. 159°-60° C. Alternatively, the title compound may be obtained in a 70% yield by treating at 200°-250° C with about 1.5 equimolecular proportion of sulfur.

Workup

  1. temperatureThe mixture is refluxed for about three hours
  2. temperatureRefluxing
  3. waitto stand overnight
  4. temperaturethe resulting suspension is refluxed for 8 hours
  5. temperatureAfter cooling
  6. filtrationthe solid catalyst is filtered off
  7. dry with materialthe benzene solution is dried under vacuum
  8. customa residue is obtained which
  9. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-384101d701fd4c97b6c46262de751977
Source dataset
uspto-grants-1978_02
Patent number
US04075341

Reaction notes

Loading…