Ethyl Acetate → 3-Aminobenzo[e][1,2,4]triazin-7-ol

HRID 387424Notes

Reaction equation

HRID 387424 reaction equation
[NH2:1][C:2]1[N:3]=[N+:4]([O-])[C:5]2[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=2[N:7]=1.C(OCC)(=O)C>CN(C)C=O.CO.[Pd]>[NH2:1][C:2]1[N:3]=[N:4][C:5]2[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 178508192HCID 178508192, compound

Product 1

HCID 1357412373-Aminobenzo[e][1,2,4]triazin-7-olYield 76.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

4.6 g (25.82 mmol) of 3-amino-benzo[1,2,4]triazine-7-ol-1-oxide was dissolved in 200 mL of 1:1 mixture of dimethylformamide and methanol. 0.5 g of 10% Pd/C was added to this solution and H2 gas was bubbled through the solution for 3 hours. The progress of the reaction was monitored by TLC, using a 9:1 mixture of dichloromethane/methanol as an eluent and a UV lamp. The starting material is highly fluorescent under UV, while the product is not. When the reaction was complete, the resulting dark solution was filtered through a short pad of silica gel and solvent was removed in vacuum to produce a dirty-brown solid. 40 mL of ethyl acetate and 40 mL of methanol were added to the solid and the resulting suspension was heated to reflux for about 10 min. Then the suspension was allowed to cool down to ambient temperature. The solid was collected by filtration, washed with 40 mL of ethyl acetate, 40 mL of diethyl ether and dried in vacuum to yield 3.2 g of the product in a form of a greenish solid. Yield: 76%.

Workup

  1. customwas bubbled through the solution for 3 hours
  2. additiona 9:1 mixture of dichloromethane/methanol as an eluent
  3. filtrationthe resulting dark solution was filtered through a short pad of silica gel and solvent
  4. customwas removed in vacuum
  5. customto produce a dirty-brown solid
  6. temperaturethe resulting suspension was heated
  7. temperatureto reflux for about 10 min
  8. filtrationThe solid was collected by filtration
  9. washwashed with 40 mL of ethyl acetate, 40 mL of diethyl ether
  10. customdried in vacuum

Sources & evidence

ORD record
ord-5a6d5edf3e0f4c08ab84be1e960d70ab
Source dataset
uspto-grants-2013_02
Patent number
US08372971B2

Reaction notes

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