Methane → 4,5-Dihydrotetrazolo[1,5-a]quinoxaline

HRID 1576012Notes

Reaction equation

HRID 1576012 reaction equation
[N:1]1[N:5]2[C:6]3[C:11]([N:12]=[CH:13][C:4]2=[N:3][N:2]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3.C.[H][H]>C(O)C>[N:1]1[N:5]2[C:6]3[C:11]([NH:12][CH2:13][C:4]2=[N:3][N:2]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

5

Reactant 3

HCID 297MethaneHCID 10103592HCID 10103592, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 215140494,5-Dihydrotetrazolo[1,5-a]quinoxalineYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 1 g. portion of tetrazolo[1,5-a]quinoxaline was dissolved in 200 ml. of ethanol. The solution was placed in a Parr hydrogenator on a shaking apparatus and 100 mg. of 5 percent palladized charcoal was added. The bomb was pressurized to about 2 atmospheres with hydrogen and was shaken for 2 hours. The reaction mixture was then removed and filtered. The filtrate was evaporated to dryness and the residue was recrystallized from ethanol-water to obtain the product, 4,5-dihydrotetrazolo[1,5-a]quinoxaline, m.p. 149°-51°C., in 45 percent yield. The product was identified by nuclear magnetic resonance analysis and by elemental microanalysis, with the following results.

Workup

  1. additionwas added
  2. customThe reaction mixture was then removed
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-bd0f956c3b6b459aaedcceb9ea95ca2e
Source dataset
uspto-grants-1976_09
Patent number
US03979387

Reaction notes

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