Methyl iodide → 1H-Indole, 2,3-dihydro-1-methyl-5-nitro-

Temperature

23 °C

25 ml of anhydrous DMF is introduced into a 150 ml three-necked flask, under an inert atmosphere, followed by 0.84 g (21 mmol) of 60% NaH. The reaction mixture is cooled down using an ice bath before the dropwise addition of a solution of 3.28 g (20 mmol) of 5-nitroindoline in 5 ml of anhydrous DMF. At the end of the addition, agitation is maintained for 1 hour at 23° C., before introducing dropwise a solution of 1.31 ml (21 mmol) of MeI in 5 ml of anhydrous DMF. Agitation is continued for 15 hours at 23° C. The reaction is finally neutralized, at 0° C., with 20 ml of a saturated solution of NH4Cl. The reaction mixture is then diluted with 20 ml of water and 50 ml of AcOEt. After decanting, the organic phase is washed successively with 20 ml of water then 20 ml of salt water, dried over magnesium sulphate, filtered and concentrated under vacuum. A dark yellow powder is obtained.

1. temperatureThe reaction mixture is cooled down
2. additionAt the end of the addition, agitation
3. customAfter decanting
4. washthe organic phase is washed successively with 20 ml of water
5. dry with material20 ml of salt water, dried over magnesium sulphate
6. filtrationfiltered
7. concentrationconcentrated under vacuum
8. customA dark yellow powder is obtained

ORD record

ord-aeefd9e375bd49a69f5f9160e457481a

Source dataset

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06821986B2