Ethyl Bromide → HCID 69071675, compound

HRID 2374475Notes

Reaction equation

HRID 2374475 reaction equation
[CH3:1][C:2]1([CH3:15])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:14].[H-].[Na+].Br[CH2:19][CH3:20]>CN(C)C=O>[CH2:19]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=2)[C:2]([CH3:15])([CH3:1])[C:3]1=[O:14])[CH3:20]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 135892273,3-Dimethyl-6-nitro-1,3-dihydro-2H-indol-2-one

Product 1

HCID 69071675HCID 69071675, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one (6 g, 29.10 mmol) in anhydrous N,N-dimethylformamide (DMF) (35 ml) was treated with sodium hydride. The resulting suspension was stirred for 1 h at 60° C. A solution of bromo-ethane (2.17 mL, 3.17 g, 29.10 mmol) in DMF (10 ml) was added. The mixture was allowed to cool to room temperature and stirred for 1 h. After removal of the solvent the mixture was quenched with water (100 ml) and extracted with ethyl acetate (3×100 ml). The extract was dried over Na2SO4, evaporated and the crude product was purified by column chromatography on silica gel. Elution with ethyl acetate/n-heptane (1:3) yielded 5.94 g (87%) of a yellow solid.

Workup

  1. temperatureto cool to room temperature
  2. stirringstirred for 1 h
  3. customAfter removal of the solvent the mixture
  4. customwas quenched with water (100 ml)
  5. extractionextracted with ethyl acetate (3×100 ml)
  6. dry with materialThe extract was dried over Na2SO4
  7. customevaporated
  8. customthe crude product was purified by column chromatography on silica gel
  9. washElution with ethyl acetate/n-heptane (1:3)

Sources & evidence

ORD record
ord-e8530b8b78884fb8aba16e8c3cb04d5b
Source dataset
uspto-grants-2008_12
Patent number
US07462639B2

Reaction notes

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