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

HRID 1502110Notes

Reaction equation

HRID 1502110 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[N:15][N:14]=[N:13]2)=[CH:8][N:7]=1)C.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[N:12]1([C:9]2[CH:10]=[CH:11][C:6]([CH2:5][C:4]([OH:17])=[O:3])=[N:7][CH:8]=2)[CH:16]=[N:15][N:14]=[N:13]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-9ff4921b84124491b29e21743c89ac43
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

Loading…