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

HRID 1502105Notes

Reaction equation

HRID 1502105 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][C:6]1[CH:7]=[N:8][C:9]([N:12]2[CH:16]=[N:15][N:14]=[N:13]2)=[CH:10][CH:11]=1)C.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[N:12]1([C:9]2[N:8]=[CH:7][C:6]([CH2:5][C:4]([OH:17])=[O:3])=[CH:11][CH:10]=2)[CH:16]=[N:15][N:14]=[N:13]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-478f49347ac04b92ada7070226834329
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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