Water → 4-Pyridin-4-yl-1,3-dihydro-indol-2-one

HRID 1826710Notes

Reaction equation

HRID 1826710 reaction equation
[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[N:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:29]=2[CH:30]=[CH:31][NH:32]3)=[CH:24][CH:23]=1.[OH2:37]>CC(O)(C)C.C(O)C.C(O)(=O)C.[Zn]>[N:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:29]=2[CH2:30][C:31](=[O:37])[NH:32]3)=[CH:24][CH:23]=1

Participants

8

Reactant 3

HCID 962WaterHCID 21124087PyridiniumtribromideHCID 221354354-(Pyridin-4-yl)-1H-indole

Product 1

HCID 121115814-Pyridin-4-yl-1,3-dihydro-indol-2-oneYield 99%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×HCID 702EthanolSolventHCID 6386tert-ButanolSolvent

Procedure

Pyridinium tribromide (90% (Aldrich), 24.70 g, 69.50 mmol) was added portion-wise over 10 minutes to a suspension of 4-pyridin-4-yl-1H-indole (4.50 g, 23.17 mmol) in 2-methyl-2-propanol (135 mL), ethanol (90 mL) and acetic acid (45 mL). The mixture was stirred at room temperature for one hour and then acetic acid (180 mL) was added. After stirring for an additional hour, water (1 mL) and zinc dust (15.06 g, 232 mmol) were added and stirring was continued for another hour. Residual zinc dust was removed by filtration and washed with methanol. The filtrate was concentrated and the syrupy residue was stirred in water (500 mL) overnight. The solid that formed was filtered, washed with water to remove zinc and pyridine salts and dried under high vacuum dry to give 5.85 g (99%) of 4-pyridin-4-yl-1,3-dihydroindol-2-one as a light yellow solid.

Workup

  1. stirringAfter stirring for an additional hour
  2. stirringstirring
  3. waitwas continued for another hour
  4. customResidual zinc dust was removed by filtration
  5. washwashed with methanol
  6. concentrationThe filtrate was concentrated
  7. stirringthe syrupy residue was stirred in water (500 mL) overnight
  8. customThe solid that formed
  9. filtrationwas filtered
  10. washwashed with water
  11. customto remove zinc and pyridine salts
  12. customdried under high vacuum
  13. customdry

Sources & evidence

ORD record
ord-a427e53113d54df9b30f623f6b5d571e
Source dataset
uspto-grants-2006_05
Patent number
US07053086B2

Reaction notes

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