1-(3,3-Dimethyl-6-nitroindolin-1-yl)ethanone → 3,3-Dimethyl-6-nitroindoline

HRID 2356965Notes

Reaction equation

HRID 2356965 reaction equation
[CH3:1][C:2]1([CH3:17])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[N:4](C(=O)C)[CH2:3]1>O1CCOCC1.Cl>[CH3:1][C:2]1([CH3:17])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[NH:4][CH2:3]1

Participants

4

Reactant 1

HCID 161274181-(3,3-Dimethyl-6-nitroindolin-1-yl)ethanone

Product 1

HCID 219594663,3-Dimethyl-6-nitroindoline

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

2 g 1-(3,3-dimethyl-6-nitro-2,3-dihydro-indol-1-yl)-ethanone were dissolved in a mixture of 6 ml dioxane and 6 ml of an aqueous 2 N solution of hydrochloric acid in a process vial. The vial was sealed with a teflon septum and placed in the microwave cavity. The reaction mixture was stirred for 15 minutes at 120° C. by microwave-assisted heating (Emrys Optimizer, Personal Chemistry). After removal of the solvent under reduced pressure the residue was treated with an aqueous saturated solution of sodium carbonate and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. Filtration and concentration of the solvent under reduced pressure yielded a white solid.

Workup

  1. temperatureby microwave-assisted heating (Emrys Optimizer, Personal Chemistry)
  2. customAfter removal of the solvent under reduced pressure the residue
  3. additionwas treated with an aqueous saturated solution of sodium carbonate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationFiltration and concentration of the solvent under reduced pressure
  7. customyielded a white solid

Sources & evidence

ORD record
ord-e66fb15b764242bdb6dbe1ebc2090c59
Source dataset
uspto-grants-2010_07
Patent number
US07759379B2

Reaction notes

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