Sodium Hydroxide → 2-phenyl-2H-1,2,3,4-tetrazole-5-carboxylic acid

HRID 1755228Notes

Reaction equation

HRID 1755228 reaction equation
[C:1]1([N:7]2[N:11]=[N:10][C:9]([C:12]([O:14]CC)=[O:13])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CCO.O>[C:1]1([N:7]2[N:11]=[N:10][C:9]([C:12]([OH:14])=[O:13])=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67258721ethyl 2-phenyl-2H-tetrazole-5-carboxylate

Product 1

HCID 1431982-phenyl-2H-1,2,3,4-tetrazole-5-carboxylic acidYield 56.4%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 2-phenyl-2H-tetrazole-5-carboxylate (0.84 g, 3.9 mmol, 1 eq) in 7.6 mL of EtOH/H2O (1.5:1) was added NaOH (0.31 g, 7.8 mmol, 2 eq). The reaction mixture was heated at 60° C. for 30 min and was then quenched with 0.65 mL of conc. HCl. The contents were filtered and washed with MeOH and the filtrate was dried with Na2SO4 and concentrated in vacuo. Purification by silica gel flash chromatography (100% EtoAc) afforded 2-phenyl-2H-tetrazole-5-carboxylic acid (0.41 g, 2.2 mmol, 55%).

Workup

  1. customwas then quenched with 0.65 mL of conc. HCl
  2. filtrationThe contents were filtered
  3. washwashed with MeOH
  4. dry with materialthe filtrate was dried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel flash chromatography (100% EtoAc)

Sources & evidence

ORD record
ord-80fc076aebdb4cc1aa4b41720d74572d
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

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