Methyl iodide → HCID 11775597, compound

Temperature

-78 °C

A mixture of 7-nitro 1-tetralone (1.91 g, 10 mmol) in 15 mL of THF was cooled to −78° C., treated dropwise with 2M lithium diisopropylamine (15 mL, 30 mmol), stirred at −78° C. for 15 minutes, treated with methyl iodide (3.11 mL, 50 mmol), stirred at −78° C. for 10 minutes, warmed to room temperature, and stirred overnight. The mixture was quenched with 10% ammonium chloride and treated with ethyl acetate. The organic phase was washed with brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography eluting with 10% ethyl acetate in n-hexane to provide the desired product. MS (ESI(−)) m/e 218 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 8.56 (d, 1H), 8.34-8.38 (d, 1H), 7.67 (d, 1H), 3.11 (t, 2H), 1.99 (t, 2H), 1.16 (s, 6H).

1. stirringstirred at −78° C. for 10 minutes
2. temperaturewarmed to room temperature
3. stirringstirred overnight
4. customThe mixture was quenched with 10% ammonium chloride
5. additiontreated with ethyl acetate
6. washThe organic phase was washed with brine
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe crude product was purified by silica gel column chromatography
11. washeluting with 10% ethyl acetate in n-hexane

ORD record

ord-8c3f17ca9c0e42df863fe72e99e76ffc

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07491718B2