Isatin → HCID 13007328, compound

HRID 1417927Notes

Reaction equation

HRID 1417927 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[H-].[Na+].[H][H].[O:16]1[CH2:20][CH2:19][O:18][CH:17]1[C:21]1[CH:22]=[C:23](Br)[CH:24]=[CH:25][CH:26]=1>C(Cl)(Cl)Cl>[O:16]1[CH2:20][CH2:19][O:18][CH:17]1[C:21]1[CH:26]=[C:25]([N:1]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4](=[O:5])[C:2]2=[O:3])[CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 7054IsatinHCID 24758Sodium hydrideHCID 873062-(3-Bromophenyl)-1,3-dioxolaneHCID 178418361HCID 178418361, compound

Product 1

HCID 13007328HCID 13007328, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
150 °C

Procedure

A solution of isatin (5.0 g, 34.0 mmol) in anhydrous N. N-dimethyl formamide (150 ml) was treated with sodium hydride (60% dispersion, 1.632 g, 40.8 mmol) with stirring at room temperature for 20 minutes until the formation of hydrogen gas ceased. To the mixture was added cupric iodide (12.9 g, 68.0 g) followed by 3-(1,3-dioxolan-2-yl)bromobenzene (15.57 g, 68.0 mmol). After 8 hours of stirring at 150° C. under nitrogen, the brown mixture was cooled to room temperature, and then treated with chloroform (750 ml). The resulting mixture was filtered to remove the precipitate. The filtrate was evaporated under reduced pressure to dryness to afford a brown solid.

Workup

  1. temperaturethe brown mixture was cooled to room temperature
  2. filtrationThe resulting mixture was filtered
  3. customto remove the precipitate
  4. customThe filtrate was evaporated under reduced pressure to dryness
  5. customto afford a brown solid

Sources & evidence

ORD record
ord-8649c3e1789f4d549102d861c666f60e
Source dataset
uspto-grants-1999_03
Patent number
US05879894

Reaction notes

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