Methyl iodide → HCID 70895875, compound

HRID 1519046Notes

Reaction equation

HRID 1519046 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:17])[C:11]([Cl:16])=[C:12]([CH3:15])[NH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18](=O)([O-])[O-].[K+].[K+].IC.C(OCC)(=O)C>CN(C=O)C.O>[CH2:1]([O:8][C:9]1[C:10](=[O:17])[C:11]([Cl:16])=[C:12]([CH3:15])[N:13]([CH3:18])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 70895895HCID 70895895, compound

Product 1

HCID 70895875HCID 70895875, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5-(Benzyloxy)-3-chloro-2-methylpyridin-4(1H)-one (3.00 g, 12.0 mmol) was suspended in 25 mL of DMF. Potassium carbonate (3.30 g, 24.0 mmol) was added followed by the addition of iodomethane (1.53 mL, 24.0 mmol). The progress of the reaction was monitored by TLC (30% ethyl acetate in hexanes). Upon completion, the reaction was allowed to stir at room temperature. Water was added and a white precipitate formed. The solid was collected by suction filtration, allowed to air dry and then further dried under vacuum. Thus, 5-(benzyloxy)-3-chloro-1,2-dimethylpyridin-4(1H)-one (2.00 g) was obtained. Yield=63%; 1H NMR (MeOD-D4, 90 MHz,) δ (ppm): 7.61 (s, 1H), 7.27-7.46 (m, 5H), 5.21 (s, 2H), 3.75 (s, 3H) and 2.54 (s, 3H).

Workup

  1. customa white precipitate formed
  2. filtrationThe solid was collected by suction filtration
  3. customto air dry
  4. customfurther dried under vacuum

Sources & evidence

ORD record
ord-59c9101cfb6f4d5f8c03bd170f5fe3a1
Source dataset
uspto-grants-2015_07
Patent number
US09073865B2

Reaction notes

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