Hydrochloric Acid → 2-Oxo-1-phenyl-1,2-dihydropyridine-3-carboxylic acid

HRID 2374024Notes

Reaction equation

HRID 2374024 reaction equation
[O:1]=[C:2]1[C:7]([C:8]([O:10]C)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Li+].[OH-].CCOC(C)=O.Cl>CO.O>[O:1]=[C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 59852857Methyl 2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxylate

Product 1

HCID 210815852-Oxo-1-phenyl-1,2-dihydropyridine-3-carboxylic acidYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxylate (70 mg, 0.31 mmol) and LiOH (40 mg) in methanol (6 mL) and water (1 mL) was stirred at rt overnight. To the reaction mixture were added EtOAc (50 mL) and 1 N aq HCl (15 mL). The EtOAc layer was separated, dried over MgSO4, and concentrated in vacuo to afford the product (55 mg, 83%) as a light yellow solid. 1H NMR (DMF-d7) δ 11.77 (br s, 1H), 8.57 (dd, 1H, J=7.4, 2.0 Hz), 8.26 (dd, 1H, J=6.6, 1.6 Hz), 7.64-7.55 (m, 5H), 6.88 (t, 1H, J=7.0 Hz); MS(ESI+) m/z 216.2 (M+H)+.

Workup

  1. customThe EtOAc layer was separated
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-790735bfca9a49cf917da642f4397d17
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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