Hydrochloric Acid → HCID 28492531, compound

HRID 571234Notes

Reaction equation

HRID 571234 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]2=[O:14])([O-:3])=[O:2].[H-].[Na+].Br[CH2:18][C:19]([O:21][CH3:22])=[O:20].Cl>CN(C=O)C.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:8](=[O:13])[C:7]2=[O:14])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 46692505-Nitroisatin

Product 1

HCID 28492531HCID 28492531, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-nitroindoline-2,3-dione (1 g, 5.20 mmol) in DMF (20 ml) was cooled to 0° C., and NaH (60% w/w dispersion in mineral oil, 0.208 g, 5.20 mmol) was added portion wise. The mixture was stirred at 0° C. for 1 hour, and methyl 2-bromoacetate (0.483 ml, 5.20 mmol) was added. The mixture was stirred at room temperature for 4 hours, then it was portioned between ethyl acetate and 1N HCl. The organic phase was washed twice with brine and dried over sodium sulfate. The solvent was removed and the crude was purified by flash chromatography on silica gel (DCM:EtOAc=95:5) affording methyl 2-(5-nitro-2,3-dioxoindolin-1-yl)acetate (0.976 g, 3.69 mmol, 71% yield) MS/ESI+ 264.9 [MH]+.

Workup

  1. stirringThe mixture was stirred at room temperature for 4 hours
  2. washThe organic phase was washed twice with brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed
  5. customthe crude was purified by flash chromatography on silica gel (DCM:EtOAc=95:5)

Sources & evidence

ORD record
ord-b15db9228dfb43a3b866a93d6ca2f721
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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