Water → HCID 178515415, compound

HRID 2383165Notes

Reaction equation

HRID 2383165 reaction equation
[O-]CC.[K+].[CH2:5]([O:12][C:13]1[CH:14]=[CH:15][C:16]([N:24]2[C:28]([CH3:29])=[N:27][N:26]=[N:25]2)=[C:17]([CH:23]=1)[C:18]([O:20]CC)=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O.[Cl-].[NH4+]>CN(C=O)C>[CH2:5]([O:12][C:13]1[CH:23]=[C:17]2[C:16](=[CH:15][CH:14]=1)[N:24]1[N:25]=[N:26][N:27]=[C:28]1[CH:29]=[C:18]2[OH:20])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 23670592Potassium ethoxideHCID 67051161Ethyl 5-benzyloxy-2-(5-methyltetrazol-1-yl)benzoate

Product 1

HCID 178515415HCID 178515415, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium ethoxide (57.5 g, 0.682 mol) was added portionwise to a solution of ethyl 5-benzyloxy-2-(5-methyltetrazol-1-yl)benzoate (115.6 g, 0.341 mol) in 550 mL of DMF. The reaction exothermed and the temperature increased by 35 degrees. The reaction mixture was cooled in an ice bath and stirred for 1 hour. The solution was then poured into 6 L of water containing 500 g of ammonium chloride. A yellow-orange precipitate formed. After stirring overnight, the reaction was filtered. The recovered solid was dried at 50° C. in a vacuum oven to provide 100 g of 7-(benzyloxy)tetraazolo[1,5-a]quinolin-5-ol.

Workup

  1. temperatureThe reaction exothermed and the temperature increased by 35 degrees
  2. temperatureThe reaction mixture was cooled in an ice bath
  3. customA yellow-orange precipitate formed
  4. stirringAfter stirring overnight
  5. filtrationthe reaction was filtered
  6. customThe recovered solid was dried at 50° C. in a vacuum oven

Sources & evidence

ORD record
ord-9b1924cc2cbe43bda1957b213c539b3a
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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