Potassium Iodide → (+/-)-Ethyl methyl 2,2'-(4-nitro-2,3-dihydro-1H-indole-1,3-diyl)diacetate

HRID 1696358Notes

Reaction equation

HRID 1696358 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH2:7][NH:8]2)([O-:3])=[O:2].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>CC(C)=O>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH2:7][N:8]2[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7748Ethyl bromoacetateHCID 10340Sodium CarbonateHCID 10243182methyl (4-nitro-2,3-dihydro-1H-indol-3-yl)-acetate

Product 1

HCID 59257866(+/-)-Ethyl methyl 2,2'-(4-nitro-2,3-dihydro-1H-indole-1,3-diyl)diacetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (±)-methyl (4-nitro-2,3-dihydro-1H-indol-3-yl)acetate from Step B (700 mg, 2.97 mmol), sodium carbonate (471 mg, 4.44 mmol), and potassium iodide (98 mg, 0.59 mmol) in acetone (15 mL) was added ethyl bromoacetate (9.9 mL, 88.9 mmol). The mixture was heated at reflux for 18 h, then cooled to ambient temperature and concentrated in vacuo. The residue was partitioned between H2O (15 mL) and EtOAc (2×40 mL) and the organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to a volume of 50 mL. Hexane was added to the EtOAc solution and a precipitate formed. The desired crystals were collected by vacuum filtration to give the title compound. MS: m/z=323 (M+1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between H2O (15 mL) and EtOAc (2×40 mL)
  5. washthe organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to a volume of 50 mL
  9. additionHexane was added to the EtOAc solution
  10. customa precipitate formed
  11. filtrationThe desired crystals were collected by vacuum filtration

Sources & evidence

ORD record
ord-cba5a4f7cc3d4407966185ac661102bb
Source dataset
uspto-grants-2012_04
Patent number
US08163752B2

Reaction notes

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