Hydrochloric Acid → (R)-1-(2-hydroxypropyl)-6-oxo-1,6-dihydropyridine-3-carboxylic acid

HRID 2370815Notes

Reaction equation

HRID 2370815 reaction equation
[OH:1][C@H:2]([CH3:15])[CH2:3][N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]([O:13]C)=[O:12])=[CH:5]1.[OH-].[Na+].Cl>O1CCOCC1.CO>[OH:1][C@H:2]([CH3:15])[CH2:3][N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]([OH:13])=[O:12])=[CH:5]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71165424(R)-methyl 1-(2-hydroxypropyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

Product 1

HCID 86687984(R)-1-(2-hydroxypropyl)-6-oxo-1,6-dihydropyridine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
23 °C

Procedure

A solution of (R)-methyl 1-(2-hydroxypropyl)-6-oxo-1,6-dihydropyridine-3-carboxylate (508 mg, 2.405 mmol) in 1,4-dioxane (12 mL) and MeOH (4.00 mL) was treated with aqueous sodium hydroxide, 5.0 M (0.962 mL, 4.81 mmol). The reaction was stirred at 23° C. After 20 h, the reaction was neutralized to pH=6.0 with 2 N HCl, and concentrated in vacuo. The residue was azeotroped with toluene (3×10 mL), suspended in a 1:1 MeOH:DCM solution (25 mL), and the white NaCl residue was removed by filtration. The filtrate was concentrated, affording (R)-1-(2-hydroxypropyl)-6-oxo-1,6-dihydropyridine-3-carboxylic acid as a white solid. MS (ESI pos. ion) m/z: 198.1 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was azeotroped with toluene (3×10 mL)
  3. customDCM solution (25 mL), and the white NaCl residue was removed by filtration
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-4e4a37164b8f47c9a8f0c6719576db94
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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