Methyl iodide → 2,5-Dimethoxy-N-methylaniline

온도

40 °C

To a 100 mL three neck round bottom flask was added 2,5-dimethoxyaniline (1.53 g), anhydrous potassium carbonate (1.66 g), acetonitrile (25 mL) and iodomethane (1.42 g). The reaction mixture was stirred at 40° C. for 3 days under nitrogen in the dark. The reaction mixture was quenched with ethyl acetate (50 mL) and filtered. The residue was washed with ethyl acetate (3×20 mL). The filtrate and the washings were combined and washed with water (3×30 mL). The organic layer was filtered through MgSO4 and evaporated under reduced pressure. The residue was dissolved in a minimum amount of ethyl acetate/hexane 1:8. The solution was placed on a wet column of silica gel (80 g) and eluted with ethyl acetate/hexane: 300 mL (1:8), 500 mL (1:5) to afford 0.51 g of N-methyl-2,5-dimethoxyaniline. To a 50 mL three neck round bottom flask with compound 117 (0.32 g, 1.61 mmol), N-methyl-2,5-dimethoxyaniline (0.40 g) and anhydrous potassium carbonate (0.27 g) was added anhydrous DMSO (3 mL) and the reaction mixture stirred at 45° C. for 8 h under nitrogen in the dark. Distilled water (10 mL) was added to precipitate the product and the suspension stirred for 2 h and then cooled to 5° C. and filtered. The solid was washed with cold water (2×2 mL) suspended in MeOH (200 mL). Silica gel (1 g) was added and the suspension sonicated and then heated to 50° C. for 15 min. The suspension was then evaporated under reduced pressure and dried in vacuo at room temperature for 10 h. The residue was powdered and poured on top of a wet column of silica gel (40 g) and eluted with 5% of MeOH in CHCl3. Fractions corresponding the product spot (TLC) were pooled and evaporated. The residue was washed with ether and air dried to afford 0.15 g (28%) of compound 434 as a white solid.

1. customThe reaction mixture was quenched with ethyl acetate (50 mL)
2. filtrationfiltered
3. washThe residue was washed with ethyl acetate (3×20 mL)
4. washwashed with water (3×30 mL)
5. filtrationThe organic layer was filtered through MgSO4
6. customevaporated under reduced pressure
7. dissolutionThe residue was dissolved in a minimum amount of ethyl acetate/hexane 1:8
8. washeluted with ethyl acetate/hexane

ORD 기록

ord-1c9c2c2a493040b088640f3ac19bd157

출처 데이터셋

uspto-grants-1999_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05958930