Phosphoric Acid → [6-(1H-Tetrazol-1-yl)pyridine-3-yl]acetic acid

HRID 2173317Notes

Reaction equation

HRID 2173317 reaction equation
[N:1]1([C:6]2[N:11]=[CH:10][C:9]([CH2:12][C:13]([O:15]CC)=[O:14])=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.[OH-].[Na+].OP(O)(O)=O>O>[N:1]1([C:6]2[N:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 14798Sodium HydroxideHCID 77230693ethyl [6-(1H-tetrazol-1-yl)pyridin-3-yl]acetate

Product 1

HCID 66524945[6-(1H-Tetrazol-1-yl)pyridine-3-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of ethyl [6-(1H-tetrazol-1-yl)pyridin-3-yl]acetate (30.0 g, 129 mmol) in 150 mL of water was added 28 mL of 5M aq NaOH (141 mmol) over 5 min while cooled in a water bath. A very mild exotherm to +22° C. was observed. The mixture was stirred for 40 min at rt whereupon 106 mL of 2M aq H3PO4 was added over 30 min at rt. The resulting suspension was filtered, and the filter cake was washed with 2×50 mL water and dried on the frit under a stream of nitrogen overnight to afford [6-(1H-tetrazol-1-yl)pyridin-3-yl]acetic acid. This material was identical by H NMR to that synthesized according to method 1 above.

Workup

  1. temperaturewhile cooled in a water bath
  2. customto +22° C.
  3. additionwas added over 30 min at rt
  4. filtrationThe resulting suspension was filtered
  5. washthe filter cake was washed with 2×50 mL water
  6. customdried on the frit under a stream of nitrogen overnight

Sources & evidence

ORD record
ord-8a514f9bd9034d5bad0bee9d3cd87c68
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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