Water → ethyl 4-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)butanoate

HRID 2410400Notes

Reaction equation

HRID 2410400 reaction equation
[N:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])[NH:3][N:2]=1.Br[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[O:11]=[C:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:1]=[N:2][N:3]1[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 1354087931,2,3-Benzotriazin-4(1H)-one

Product 1

HCID 60262901ethyl 4-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)butanoateYield 76.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a dry round bottom flask, 1,2,3-benzotriazin-4(3H)-one (50 g), ethyl 4-bromobutanoate (86.2 g) and potassium carbonate (141 g) were taken and dissolved in dimethylformamide (350 mL) and heated to 60° C. to 70° C. for 3 to 4 hours. After cooling to room temperature, water was added to the reaction mixture and extracted with ethyl acetate. The combined organic layer was washed with water and brine and dried over anhydrous sodium sulfate. Solvents were evaporated under reduced pressure and the crude product was purified by silica gel flash column chromatography over silica gel using 20% ethylacetate in hexane as eluant to afford the title compound (68 g).

Workup

  1. temperatureheated to 60° C. to 70° C. for 3 to 4 hours
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customSolvents were evaporated under reduced pressure
  6. customthe crude product was purified by silica gel flash column chromatography over silica gel using 20% ethylacetate in hexane as eluant

Sources & evidence

ORD record
ord-0b5e031adf714d8a9ff2e131ff19cd11
Source dataset
uspto-grants-2014_08
Patent number
US08816073B2

Reaction notes

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