Dimethylamine → {2-[3,3-dimethyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}dimethylamine

HRID 1014282Notes

Reaction equation

HRID 1014282 reaction equation
[CH3:1][C:2]1([CH3:16])[C:10]2[C:5](=[CH:6][C:7]([N+:13]([O-:15])=[O:14])=[C:8]([O:11][CH3:12])[CH:9]=2)[NH:4][CH2:3]1.[CH3:17][CH2:18][N:19]([CH:23](C)C)[CH:20](C)C.BrCC(Cl)=[O:29].CNC.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:1][C:2]1([CH3:16])[C:10]2[C:5](=[CH:6][C:7]([N+:13]([O-:15])=[O:14])=[C:8]([O:11][CH3:12])[CH:9]=2)[N:4]([C:17](=[O:29])[CH2:18][N:19]([CH3:23])[CH3:20])[CH2:3]1

Participants

7

Reactant 5

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 89602Bromoacetyl chlorideHCID 516892Sodium BicarbonateHCID 594418113,3-dimethyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole

Product 1

HCID 59441896{2-[3,3-dimethyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}dimethylamineYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3,3-dimethyl-5-(methyloxy)-6-nitro-2,3-dihydro-1 H-indole (2.38 g, 10.71 mmol), Hunig's base (9.33 mL, 53.5 mmol) and bromo-acetylchloride (1.159 mL, 13.92 mmol) in tetrahydrofuran (100 mL) was maintained at 0° C. for 2 hours. Dimethylamine (2.0M in THF, 42.8 mL, 86 mmol) was added to the solution and the reaction was warmed to room temperature and maintained for 5 hours. The reaction was poured into saturated sodium bicarbonate, the organic layer was dried over sodium sulfate, filtered, and purified by column chromatography to afford {2-[3,3-dimethyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}dimethylamine (2.14 g, 65.0% yield) as an orange solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.44 (s, 1 H), 7.35 (s, 1 H), 3.97 (s, 2 H), 3.92 (s, 3 H), 3.21 (s, 2 H), 2.26 (s, 6H), 1.34 (s, 6 H).

Workup

  1. temperaturemaintained for 5 hours
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-de897e74470743a6b12e7e3e8ec41d36
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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