反应详情

温度

65 °C

A suspension of {2-[3,3-dimethyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}dimethylamine (2.20 g, 7.16 mmol), hydrazine hydrate (2.81 mL, 57.3 mmol), iron(III)chloride (0.232 g, 1.432 mmol), and activated carbon (2 g, 7.16 mmol) was warmed at 65° C. for 16 hours. The solution was filtered while still warm through celite, taken to a residue under reduced pressure, and partitioned between chloroform and saturated sodium bicarbonate. The organic layer was washed with saturated sodium chloride (aq), dried over sodium sulfate, filtered, taken to a residue under reduced pressure, and purified by column chromatography to afford 1-[(dimethylamino)acetyl]-3,3-dimethyl-5-(methyloxy)-2,3-dihydro-1 H-indol-6-amine (1.41 g, 71% yield) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.49 (s, 1 H), 6.69 (s, 1 H), 4.62 (s, 2 H), 3.82 (s, 2 H), 3.73 (s, 3 H), 3.12 (s, 2 H), 2.23 (s, 6 H), 1.22 (s, 6 H).

1. filtrationThe solution was filtered
2. temperaturewhile still warm through celite
3. custompartitioned between chloroform and saturated sodium bicarbonate
4. washThe organic layer was washed with saturated sodium chloride (aq)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. custompurified by column chromatography