Acetic Acid → HCID 22561961, compound

HRID 983027Notes

Reaction equation

HRID 983027 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=3)[C:13]([OH:15])=[O:14])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([OH:21])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>[O:21]=[C:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][C:5]=2[C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13]([OH:15])=[O:14])[NH:1]1

Participants

8

Reactant 4

HCID 176Acetic Acid2×HCID 702EthanolHCID 21124087PyridiniumtribromideHCID 225619543-(1H-Indol-4-yl)benzoic acid

Product 1

HCID 22561961HCID 22561961, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To the suspension of 3-(1H-indol-4-yl)-benzoic acid (7.58 g, 33 mmol) in t-BuOH: ethanol: acetic acid (150 mL: 100 mL: 50 mL) was added pyridinium tribromide (31.66 g, 99 mmol) portionwise. The mixture was stirred at room temperature for 2 hours, and then to the mixture was added with acetic acid (150 mL). Water (4 mL) and Zinc dust (13.07 g, 200 mmol) was added to the reaction mixture portionwise and stirring was continued at room temperature for 2 hours. The solvent was removed under reduced pressure. The oily residue was suspended in 1N HCl (400 mL) and stirred at room temperature overnight. The precipitate solid was collected by filtration, purified by recrystallization from ethyl acetate to give (6.4 g, 77%) of 3-(2-oxo-2,3-dihydro-1H-indol-4-yl)-benzoic acid as a pinkish white solid.

Workup

  1. stirringstirring
  2. waitwas continued at room temperature for 2 hours
  3. customThe solvent was removed under reduced pressure
  4. stirringstirred at room temperature overnight
  5. filtrationThe precipitate solid was collected by filtration
  6. custompurified by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-ed4ed3fc876e4372a2c8e07592d3601c
Source dataset
uspto-grants-2005_03
Patent number
US06861418B2

Reaction notes

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