Methyl iodide → HCID 58257133, compound

To a solution of 2-(2,5-dimethyl-4-nitrophenyl)-1H-imidazole (50 mg, 0.23 mmol) in DMF (2 mL) was added NaH (11 mg, 0.46 mmol) at 0° C. After stirring for 15 min, iodomethane (65 mg, 0.46 mmol) was added dropwise. The mixture was stirred at 0° C. for 1 hr, and quenched by adding saturated ammonium chloride aqueous solution. The mixture was extracted with ethyl acetate (3×15 mL). The organic layer was washed with brine and dried over sodium sulfate. After concentration, the residue was dissolved in methanol (10 mL). To the solution was added Pd/C (10%). The reaction mixture was degassed and purged with H2 for several times and stirred under 1 atm. hydrogen gas overnight. The mixture was filtered and concentrated to afford 2,5-dimethyl-4-(1-methyl-1H-imidazol-2-yl)aniline. ESMS m/z 202 (M+H+).

1. stirringThe mixture was stirred at 0° C. for 1 hr
2. customquenched
3. additionby adding saturated ammonium chloride aqueous solution
4. extractionThe mixture was extracted with ethyl acetate (3×15 mL)
5. washThe organic layer was washed with brine
6. dry with materialdried over sodium sulfate
7. concentrationAfter concentration
8. dissolutionthe residue was dissolved in methanol (10 mL)
9. additionTo the solution was added Pd/C (10%)
10. customThe reaction mixture was degassed
11. custompurged with H2 for several times
12. stirringstirred under 1 atm. hydrogen gas overnight
13. filtrationThe mixture was filtered
14. concentrationconcentrated

ORD record

ord-80c1959a87d5475a9082913d7e66f6e0

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08445505B2