Butyl iodide → 1-Butyl-5,6-dimethyl-3-methoxy-2-pyridone

HRID 416546Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5](=[O:9])[NH:6][C:7]=1[CH3:8].[OH-].[K+].I[CH2:15][CH2:16][CH2:17][CH3:18]>C(O)CCC>[CH2:15]([N:6]1[C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=[C:4]([O:10][CH3:11])[C:5]1=[O:9])[CH2:16][CH2:17][CH3:18]

Participants

Conditions

Temperature: 85 °C

Procedure

n-Butanol (13 mL) was added to a mixture of 5,6-dimethyl-3-methoxy-2-pyridone (1-004-06) (306 mg) and potassium hydroxide (157 mg). 1-Iodobutane (0.44 mL) was added to the suspension, and the reaction mixture was heated with stirring in an oil bath at 85° C. under nitrogen atmosphere. After 24 h, the reaction mixture was evaporated under reduced pressure, and the residue was dissolved in acetyl acetate and water. The reaction mixture was extracted twice with ethyl acetate, and once with water, dried over magnesium sulfate, and evaporated under reduced pressure. The obtained residue (300 mg) was purified by silica gel column chromatography (Lobar column B, toluene/acetone (3/1)) to give 1-butyl-5,6-dimethyl-3-methoxy-2-pyridone (1-004-07) (124 mg, 29.6%).

Workup

temperaturethe reaction mixture was heated
customthe reaction mixture was evaporated under reduced pressure
dissolutionthe residue was dissolved in acetyl acetate
extractionThe reaction mixture was extracted twice with ethyl acetate
dry with materialonce with water, dried over magnesium sulfate
customevaporated under reduced pressure
customThe obtained residue (300 mg) was purified by silica gel column chromatography (Lobar column B, toluene/acetone (3/1))

Sources & evidence

ORD record: ord-f391c593008c49f19914eda53218d2a8
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088924B2

Reaction notes

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