Acetic Acid → HCID 22561690, compound

HRID 1839628Notes

Reaction equation

HRID 1839628 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=3)[O:13][CH2:14][CH2:15][OH:16])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([OH:22])C.C(O)(=O)C.[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>CC(O)(C)C.[Zn].O>[OH:16][CH2:15][CH2:14][O:13][C:12]1[CH:11]=[C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[CH2:3][C:2](=[O:22])[NH:1]3)[CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 176Acetic Acid2×HCID 702EthanolHCID 21124087PyridiniumtribromideHCID 22561717HCID 22561717, compound

Product 1

HCID 22561690HCID 22561690, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To the suspension of 2-[3-(1H-indol-4-yl)-phenoxy]-ethanol (5.4 g, 21 mmol) in t-BuOH:ethanol:acetic acid (139.5 mL:84 mL:100.5 mL) was added pyridinium tribromide (21.21 g, 63 mmol) portionwise. The mixture was stirred at room temperature for 3 hours, and then to the mixture was added more acetic acid (90 mL) and water (3 mL). Zinc dust (21 g) was added to the reaction mixture portionwise. After stirring for one hour, the unreacted zinc was filtered off and most of the solvent was removed under reduced pressure. The residue was diluted with ethyl acetate, washed with 1N HCl (3×), water (1×), brine (2×), dried over Na2SO4, concentrated. The residue was recrystallized to give 1.82 g (32%) of 4-[3-(2-hydroxy-ethoxy)-phenyl]-1,3-dihydro-indol-2-one.

Workup

  1. stirringAfter stirring for one hour
  2. filtrationthe unreacted zinc was filtered off and most of the solvent
  3. customwas removed under reduced pressure
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with 1N HCl (3×), water (1×), brine (2×)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was recrystallized

Sources & evidence

ORD record
ord-4f5d502a5861464c874fcb5393dd05e3
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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