Acetic Acid → HCID 22561935, compound

HRID 1839621Notes

Reaction equation

HRID 1839621 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:11]=[C:12]([CH2:16][C:17]([N:19]([CH3:21])[CH3:20])=[O:18])[CH:13]=[CH:14][CH:15]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([OH:24])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>[CH3:21][N:19]([CH3:20])[C:17](=[O:18])[CH2:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[CH2:3][C:2](=[O:24])[NH:1]3)[CH:11]=1

Participants

8

Reactant 4

HCID 176Acetic Acid2×HCID 702EthanolHCID 21124087PyridiniumtribromideHCID 22561956HCID 22561956, compound

Product 1

HCID 22561935HCID 22561935, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To the suspension of 2-[3-(1H-indol-4-yl)-phenyl]-N,N-dimethyl-acetamide (1.6 g, 5 mmol) in t-BuOH:ethanol:acetic acid (332 mL:20 mL:24 mL) was added pyridinium tribromide (5 g, 15 mmol) portionwise. The mixture was stirred at room temperature for 3 hours, and then to the mixture was added acetic acid (22 mL). Water (0.7 mL) and zinc dust (5 g) were added to the reaction mixture portionwise. After stirring for one hour, any unreacted zinc was filtered off and most of the solvent was removed under reduced pressure. The residue was diluted with ethyl acetate, washed with 0.5 N HCl (2×), 10% Na2CO3 (2×), brine (2×), water, dried over Na2SO4, concentrated and triturated with ether to give N,N-dimethyl-2-[3-(2-oxo-2,3-dihydro-1H-indol-4-yl)-phenyl]-acetamide. MS m/z 293 [M−1].

Workup

  1. stirringAfter stirring for one hour
  2. filtrationany 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 0.5 N HCl (2×), 10% Na2CO3 (2×), brine (2×), water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customtriturated with ether

Sources & evidence

ORD record
ord-8afa9de8eaa943e99e2800f0001b01e1
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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