ethyl 2-(5-methyl-1H-tetrazol-1-yl)benzoate → HCID 178515414, compound

HRID 432697Notes

Reaction equation

HRID 432697 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[CH:17]=[CH:16][CH:15]=[CH:14][C:8]=2[C:9](OCC)=[O:10])[N:5]=[N:4][N:3]=1.[O-]CC.[K+]>CN(C)C=O.O>[N:5]1[N:6]2[C:7]3[C:8]([C:9]([OH:10])=[CH:1][C:2]2=[N:3][N:4]=1)=[CH:14][CH:15]=[CH:16][CH:17]=3

Participants

5

Reactant 2

HCID 3761737ethyl 2-(5-methyl-1H-tetrazol-1-yl)benzoateHCID 23670592Potassium ethoxide

Product 1

HCID 178515414HCID 178515414, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, ethyl 2-(5-methyl-1H-tetrazol-1-yl)benzoate (92.7 g, 0.34 mol) was dissolved in N,N-dimethylformamide (600 ml) and the solution was chilled in an ice water bath. Potassium ethoxide (67.2 g, 0.80 mol) was added slowly to the solution. After a few minutes, the ice water bath was removed and the reaction was stirred at room temperature for 3 hours. The reaction was treated with 100 ml of water and approximately 300-400 ml of solvent was removed in vacuo. The remainder of the reaction was poured over a solution of glacial acetic acid (125 ml) in ice water (2 L). A precipitate formed and the mixture was diluted with additional water (3 L). The solid was collected by vacuum filtration to yield 63.25 g of tetrazolo[1,5-a]quinolin-5-ol as a yellow solid.

Workup

  1. temperaturethe solution was chilled in an ice water bath
  2. waitAfter a few minutes
  3. customthe ice water bath was removed
  4. additionThe reaction was treated with 100 ml of water and approximately 300-400 ml of solvent
  5. customwas removed in vacuo
  6. additionThe remainder of the reaction was poured over a solution of glacial acetic acid (125 ml) in ice water (2 L)
  7. customA precipitate formed
  8. filtrationThe solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-101bd11f97c740388e384ecb5c3fbe23
Source dataset
uspto-grants-2003_12
Patent number
US06664260B2

Reaction notes

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