Toluene → HCID 10419796, compound

HRID 1186409Notes

Reaction equation

[I-].[O:2]1CCOC1C1C=[NH+]C=CC=1.[OH-].[K+].C1(C)C=CC=CC=1.[CH3:22][N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]2[O:33][CH2:32][CH2:31][O:30]2)[C:24]1=O>O.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[CH3:22][N:23]1[CH:24]=[C:25]([CH:29]2[O:33][CH2:32][CH2:31][O:30]2)[CH:26]=[CH:27][C:28]1=[O:2]

Participants

Conditions

Temperature: 40 °C

Procedure

3-(1,3-Dioxolan-2-yl)-1-pyridinium iodide (1.85 g, 6.31 mmol) was dissolved in water (40 mL). To this, a solution of potassium ferricyanide (22.9 g, 69.4 mmol) in water (50 mL) was added dropwise under a nitrogen atmosphere at 0° C. over 1 hour. To this, a solution of potassium hydroxide (55.9 g, 100 mmol) in water (9.5 mL) was added dropwise at the same temperature over 30 minutes. To this, toluene (65 mL) was added and the mixture was stirred at 40° C. for 30 minutes. Then, extraction with dichloromethane was performed, followed by drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by column chromatography (hexane/ethyl acetate=1/1) to give a 73:27 mixture (933 mg, yield: 82%) of 1-methyl-5-(1,3-dioxolan-2-yl)-2(1H)-pyridone and 1-methyl-3-(1,3-dioxolan-2-yl)-2(1H)-pyridone.

Workup

extractionThen, extraction with dichloromethane
dry with materialby drying over anhydrous sodium sulfate
customThe solvent was evaporated off under reduced pressure
customthe residue was purified by column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record: ord-e41b39023b5743d48bc12807ff29c4ad
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673908B2

Reaction notes

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