Dimethyl Sulfate → 6-Methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydroquinoline-7-carbaldehyde

HRID 1243983Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH:13]=[O:14])[NH:9][C:8](=[O:15])[CH2:7][CH2:6]2.[CH3:16]C(C)([O-])C.[K+].COS(OC)(=O)=O>C1COCC1.C(=O)(O)[O-].[Na+]>[CH3:16][N:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:12]([CH:13]=[O:14])[CH:11]=2)[CH2:6][CH2:7][C:8]1=[O:15]

Participants

Conditions

Temperature: 0 °C

Procedure

6-Methoxy-2-oxo-1,2,3,4-tetrahydro-quinoline-7-carbaldehyde 30 mg (0.146 mmol) was dissolved in 5 ml of anhydrous THF and the solution was cooled to 0° C. The reaction mixture was treated with 16 mg (0.146 mmol) of potassium t-butoxide whereupon it became yellow in color. After stirring for 30 minutes, the mixture was treated with 14 μl (0.146 mmol) dimethylsulfate and slowly warmed to room temperature while stirring for 16 hours. The reaction mixture was diluted with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and concentrated to an oil. The residue was chromatographed on silica gel eluting with 6/4 ethyl acetate/hexane to afford 16 mg (50%) as a white solid. MS APCI m/e 220 (p+1)

Workup

temperatureslowly warmed to room temperature
stirringwhile stirring for 16 hours
extractionextracted with ethyl acetate
dry with materialThe organic phase was dried over sodium sulfate
concentrationconcentrated to an oil
customThe residue was chromatographed on silica gel eluting with 6/4 ethyl acetate/hexane
customto afford 16 mg (50%) as a white solid

Sources & evidence

ORD record: ord-71ee6953a90e4d0db27fa7cb49b7aed4
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07119207B2

Reaction notes

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