Pyridinium hydrochloride → HCID 57912406, compound

HRID 884732Notes

Reaction equation

HRID 884732 reaction equation
CO[C:3]1[C:8]([C:9](=[O:22])[CH2:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:12])=[CH:7][CH:6]=[CH:5][N:4]=1.Cl.[NH+]1C=CC=CC=1>O>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([C:11]2[O:12][C:3]3=[N:4][CH:5]=[CH:6][CH:7]=[C:8]3[C:9](=[O:22])[CH:10]=2)=[CH:14][CH:15]=1)([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 21584435Pyridinium hydrochlorideHCID 666501871-(2-Methoxy pyridine-3-yl)-3-(4-nitrophenyl)propane-1,3-dione

Product 1

HCID 57912406HCID 57912406, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

1-(2-methoxy pyridine-3-yl)-3-(4-nitrophenyl) propane-1,3-dione (2.16 g, 7.193 mmol) and pyridinium hydrochloride (12.47 g, 107.9 mmol) were mixed together and stirred at 190° C. for 2 h under nitrogen atmosphere. The reaction mixture was cooled to rt. Water (100 mL) was added, the solid was separated by filtration, washed with water and dried under vacuum. The crude compound was purified by column chromatography (SilicaGel 230-400 mesh; 2-5% methanol in CH2Cl2 as eluent) to give 2-(4-nitrophenyl)-4H-pyrano[2,3-b]pyridine-4-one as a brown solid in 43% yield (0.82 g). MS (ES) m/z: 268.88 (M); Mp. 261-263° C.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. customthe solid was separated by filtration
  3. washwashed with water
  4. customdried under vacuum
  5. customThe crude compound was purified by column chromatography (SilicaGel 230-400 mesh; 2-5% methanol in CH2Cl2 as eluent)

Sources & evidence

ORD record
ord-c9fcb145db284287a8cbffd8e7b13fb9
Source dataset
uspto-grants-2012_08
Patent number
US08242130B2

Reaction notes

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