Calcium Carbonate → 6-amino-7-iodo-2,3-dihydro-1H-inden-1-one

HRID 1661373Notes

Reaction equation

HRID 1661373 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Ca+2].[I:17]Cl.S([O-])([O-])(=O)=S.[Na+].[Na+]>CO.O>[NH2:1][C:2]1[C:10]([I:17])=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10112Calcium CarbonateHCID 24477Sodium ThiosulfateHCID 24640Iodine chlorideHCID 3128956-amino-2,3-dihydro-1H-inden-1-one

Product 1

HCID 577812296-amino-7-iodo-2,3-dihydro-1H-inden-1-oneYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

6-Amino-1-indanone (5.00 g, 34.0 mmol) was dissolved in a mixed solvent of methanol (200 mL) and water (50 ml), calcium carbonate (6.81 g, 68.0 mmol) and iodine(I) chloride (2.22 mL, 44.2 mmol) were added, and the mixture was stirred at room temperature for 2 hr. To the reaction solution was added saturated aqueous sodium thiosulfate solution, and the organic solvent was evaporated under reduced pressure. To the mixture was added saturated aqueous sodium hydrogencarbonate solution. The mixture was extracted with ethyl acetate and washed with saturated brine. The solvent was evaporated under reduced pressure. The residue was washed with methanol and ethyl acetate to give the title compound (7.95 g, yield 86%).

Workup

  1. additionwere added
  2. customthe organic solvent was evaporated under reduced pressure
  3. additionTo the mixture was added saturated aqueous sodium hydrogencarbonate solution
  4. extractionThe mixture was extracted with ethyl acetate
  5. washwashed with saturated brine
  6. customThe solvent was evaporated under reduced pressure
  7. washThe residue was washed with methanol and ethyl acetate

Sources & evidence

ORD record
ord-47759e7dce7b4d9c8762a4f2cb257387
Source dataset
uspto-grants-2011_10
Patent number
US08030337B2

Reaction notes

Loading…