Methyl iodide → HCID 69057142, compound

HRID 1818890Notes

Reaction equation

HRID 1818890 reaction equation
O[C:2]1[N:3]=[C:4](C)[CH:5]=[C:6]2[CH2:11][CH2:10][O:9][C:8](=[O:12])[C:7]=12.[C:14](=[O:17])([O-])[O-].[K+].[K+].I[CH3:21]>CN(C)C=O>[CH3:21][O:17][CH2:14][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH2:11][CH2:10][O:9][C:8](=[O:12])[C:7]=12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178422142HCID 178422142, compound

Product 1

HCID 69057142HCID 69057142, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

8-hydroxy-6methyl-3,4-dihydro-pyrano[3,4-c]pyridine-1-on (324 mg, 1.809 mmol) and anhydrous potassium carbonate were suspended in anhydrous dimethylformamide (DMF, 10 mL) and then dropwisely added with iodomethane (1.13 mL, 18.09 mmol) and stirred for about 4 hours at 70° C. under the nitrogen atmosphere. The mixture was concentrated under reduced pressure, added with 50 mL of distilled water and then extracted six times with 40 mL of 10% MeOH/MC. The resulting organic layer was dried using anhydrous sodium sulfate, filtered and concentrated. A silica gel column chromatography (10% MeOH/MC) was performed on the resulting residue and 215 mg (62%) of 8-methoxymethyl-3,4-dihydro-pyrano[3,4-c]pyridine-1-on was obtained in pale yellow solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionadded with 50 mL of distilled water
  3. extractionextracted six times with 40 mL of 10% MeOH/MC
  4. customThe resulting organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-90e713c9962742d48e94074cf7074cac
Source dataset
uspto-grants-2009_10
Patent number
US07601736B2

Reaction notes

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