Methane → 4,6-Dimethyl-4,5-dihydrotetrazolo[1,5-a]quinoxaline

HRID 1576013Notes

Reaction equation

HRID 1576013 reaction equation
[CH3:1][C:2]1[C:3]2[N:4]([N:13]=[N:14][N:15]=2)[C:5]2[C:10]([N:11]=1)=[C:9]([CH3:12])[CH:8]=[CH:7][CH:6]=2.C>C(O)C>[CH3:1][CH:2]1[NH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH3:12])[N:4]2[N:13]=[N:14][N:15]=[C:3]12

Participants

4

Reactant 2

HCID 297MethaneHCID 21504880HCID 21504880, compound

Product 1

HCID 215140584,6-Dimethyl-4,5-dihydrotetrazolo[1,5-a]quinoxalineYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.5 g. of 4,6-dimethyltetrazolo[1,5-a]quinoxaline in 200 ml. of ethanol was hydrogenated as above at about 3 atmospheres over 150 mg. of 5 percent palladized charcoal for 17 hours. The reaction mixture was then filtered, and the filtrate was evaporated to dryness. The residue was taken up in ethyl ether and chromatographed on a silica gel column with ethyl ether as the eluting solvent. The product-containing fractions were evaporated to dryness and the residue was recrystallized from ethanol to recover 4,5-dihydro-4,6-dimethyltetrazolo[1,5-a]quinoxaline, m.p. 159°-61°C., in 81 percent yield. The product was identified by NMR analysis and by elemental analysis with the following results.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customthe filtrate was evaporated to dryness
  3. customchromatographed on a silica gel column with ethyl ether as the eluting solvent
  4. customThe product-containing fractions were evaporated to dryness
  5. customthe residue was recrystallized from ethanol
  6. customto recover 4,5-dihydro-4,6-dimethyltetrazolo[1,5-a]quinoxaline, m.p. 159°-61°C.

Sources & evidence

ORD record
ord-d399706fa09e4ad690668cec07d38d65
Source dataset
uspto-grants-1976_09
Patent number
US03979387

Reaction notes

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