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

HRID 2173314Notes

Reaction equation

HRID 2173314 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.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[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 311Citric AcidHCID 3939Lithium 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 8028TetrahydrofuranSolvent

Procedure

To a mixture ethyl [6-(1H-tetrazol-1-yl)pyridin-3-yl]acetate (0.42 g, 1.8 mmol) in THF (3 mL) was added 1.4 M LiOH (aq.) (5 mL) at room temperature. The mixture was stirred 3 hours at room temperature. The reaction was acidified with citric acid until Ph about 3˜4. The mixture was extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated to give [6-(1H-tetrazol-1-yl)pyridin-3-yl]acetic acid. 1H-NMR (400 MHz, DMSO) δ 12.62 (s, 1H), 10.16 (s, 1H), 8.54 (s, 1H), 8.01-8.09 (m, 2H), 3.80 (s, 2H).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2bdd4a9a207d4716b57f282e46596805
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

Loading…