Potassium Carbonate → HCID 89581114, compound

HRID 1500962Notes

Reaction equation

HRID 1500962 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].Br[CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:1]=[C:2]1[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=[CH:10][N:11]1[CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11454(1-Bromoethyl)benzeneHCID 178498433HCID 178498433, compound

Product 1

HCID 89581114HCID 89581114, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of methyl 2-hydroxyisonicotinate (306 mg, 2 mmol) in N,N-dimethylformamide (30 mL) was added (1-bromoethyl)benzene (0.37 g, 2 mmol) and potassium carbonate (0.55 g, 4 mmol). The mixture was heated to 110° C. and stirred at the same temperature for 12 hours. The solvent was evaporated in vacuum and the residue was purified by preparative-HPLC to give methyl 2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxylate (90 mg, 17%) The product was used directly in the next step.

Workup

  1. customThe solvent was evaporated in vacuum
  2. customthe residue was purified by preparative-HPLC

Sources & evidence

ORD record
ord-e39420d28a724f88bef6f5950689c88e
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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