Hydrochloric Acid → 2-(Pyridin-3-yloxy)acetic acid

HRID 1698346Notes

Reaction equation

HRID 1698346 reaction equation
C([O:5][C:6](=[O:15])[CH2:7][O:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)(C)(C)C.Cl>O1CCOCC1>[N:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:7][C:6]([OH:15])=[O:5])[CH:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22668053Tert-butyl 2-(3-pyridyloxy)acetate

Product 1

HCID 31596302-(Pyridin-3-yloxy)acetic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of (Pyridin-3-yloxy)-acetic acid tert-butyl ester (60 mg, 0.29 mmol) and HCl in dioxane (4 M, 2 mL) is stirred at room temperature for 1 h. The reaction mixture is concentrated in vacuo to give the title compound. MS: 154 [M+H]+; tR (HPLC, ACQUITY UPLC™ BEH C18 1.7 μm, 50×2.1 mm; 5% CH3CN+0.1% TFA/H2O+0.1% TFA for 0.5 min then 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 5 min then 100% CH3CN+0.1% TFA for 1.5 min, flow 0.5 ml/min): 0.40 min.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo

Sources & evidence

ORD record
ord-1308cae58b654c0088cdfd44a2bbdd6e
Source dataset
uspto-grants-2012_04
Patent number
US08163773B2

Reaction notes

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