Hydrochloric Acid → 2-(2-Oxopyridin-1(2H)-yl)propanoic acid

HRID 887128Notes

Reaction equation

HRID 887128 reaction equation
[O:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]1[CH:8]([CH3:16])[C:9]([O:11]C(C)(C)C)=[O:10].Cl>O1CCOCC1>[O:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]1[CH:8]([CH3:16])[C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57907642tert-butyl 2-(2-oxopyridin-1(2H)-yl)propanoate

Product 1

HCID 167879002-(2-Oxopyridin-1(2H)-yl)propanoic acidYield 99.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred suspension of 16.6 g (74.4 mmol) of tert-butyl 2-(2-oxopyridin-1(2H)-yl)propanoate from step A above in 10 mL of anhydrous 1,4-dioxane under an atmosphere of nitrogen was added 150 mL of a 4.0 M hydrogen chloride solution in 1,4-dioxane. The resulting solution was stirred overnight at ambient temperature then evaporated to dryness in vacuo to afford the title compound as a white solid (12.4 g, quantitative yield). LC-MS: m/z (ES) 168 (MH)+

Workup

  1. customthen evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-4a89850d36e14f67842ffaca6bcf3202
Source dataset
uspto-grants-2012_08
Patent number
US08247415B2

Reaction notes

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