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

HRID 1452776Notes

Reaction equation

[H-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH2:10][CH2:9]2)([O-:5])=[O:4].[CH3:15]I.[NH4+].[Cl-]>CN(C=O)C.O.CCOC(C)=O>[CH3:15][N:11]1[C:12]2[C:8](=[CH:7][C:6]([N+:3]([O-:5])=[O:4])=[CH:14][CH:13]=2)[CH2:9][CH2:10]1

Participants

Conditions

Temperature: 23 °C

Procedure

25 ml of anhydrous DMF is introduced into a 150 ml three-necked flask, under an inert atmosphere, followed by 0.84 g (21 mmole) 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 mmole) of 5-nitroindoline in 5 ml of anhydrous DMF. Once this addition is complete, agitation is maintained for 1 hour at 23° C., before the dropwise introduction of a solution of 1.31 ml (21 mmole) of MeI in 5 ml of anhydrous DMF. Agitation is maintained 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 decantation, the organic phase is washed successively with 20 ml of water, 20 ml of brine, dried over magnesium sulphate, filtered and concentrated under vacuum. A dark yellow powder is obtained.

Workup

temperatureThe reaction mixture is cooled down
additionOnce this addition
washAfter decantation, the organic phase is washed successively with 20 ml of water, 20 ml of brine
dry with materialdried over magnesium sulphate
filtrationfiltered
concentrationconcentrated under vacuum
customA dark yellow powder is obtained

Sources & evidence

ORD record: ord-e0abadd6b760410babbd0a4346d0a2c4
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473779B2

Reaction notes

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