Citric Acid → 2-(5-(1H-tetrazol-1-yl)pyridin-2-yl)acetic acid

HRID 2173325Notes

Reaction equation

HRID 2173325 reaction equation
[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([CH2:12][C:13]([O:15]CC)=[O:14])=[N:10][CH:11]=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[CH:7]=[CH:8][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[N:10][CH:11]=2)[CH:5]=[N:4][N:3]=[N:2]1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 67518188ethyl [5-(1H-tetrazol-1-yl)pyridin-2-yl]acetate

Product 1

HCID 675176762-(5-(1H-tetrazol-1-yl)pyridin-2-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture ethyl [5-(1H-tetrazol-1-yl)pyridin-2-yl]acetate (0.19 g, 0.81 mmol) in THF (4 mL) was added 1.4 M LiOH (aq.) (2.9 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 [5-(1H-tetrazol-1-yl)pyridin-2-yl]acetic acid. 1H-NMR (400 MHz, MeOD) δ 9.83 (s, 1H), 9.02 (s, 1H), 8.28 (d, J=8.8 Hz, 1H), 7.68 (d, J=8.8 Hz, 1H), 3.95 (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-3638265880224d58aaeee5dd00de65d3
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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