Hydrochloric Acid → 2-(6-methyl-5-(1H-tetrazol-1-yl)pyridin-2-yl)acetic acid

HRID 1502127Notes

Reaction equation

HRID 1502127 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([O:11]CC)=[O:10])[CH:5]=[CH:4][C:3]=1[N:14]1[CH:18]=[N:17][N:16]=[N:15]1.O.[OH-].[Li+].C(O)C.Cl>C1COCC1.O>[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:4][C:3]=1[N:14]1[CH:18]=[N:17][N:16]=[N:15]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 168937Lithium hydroxide, monohydrateHCID 89618829ethyl 2-(6-methyl-5-(1H-tetrazol-1-yl)pyridin-2-yl)acetate

Product 1

HCID 896191822-(6-methyl-5-(1H-tetrazol-1-yl)pyridin-2-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-(6-methyl-5-(1H-tetrazol-1-yl)pyridin-2-yl)acetate (310 mg, 1.25 mmol) was dissolved in THF (6 mL) and water (3 mL). Lithium hydroxide monohydrate (68.31 mg, 1.628 mmol) was added. A small amount of ethanol was also added to ensure the reaction mixture was homogeneous. After 1 hr, the reaction was acidified with 2N HCl to pH ˜5-6 then extracted with a mixture of ethyl acetate/THF (2×). The combined organic layer was dried over Na2SO4, filtered and concentrated to yield title compound: 1H-NMR (600 MHz, CDCl3) δ ppm 8.975 (s, 1H), 7.738 (d, J=8.1 Hz, 1H), 7.396 (d, J=8.1 Hz, 1H), 3.907 (s, 2H), 2.009 (s, 3H): LC-MS: M+1=220

Workup

  1. extractionthen extracted with a mixture of ethyl acetate/THF (2×)
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8448ab80c2504f159b7c919b51bcdbf2
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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