Phosphorus oxychloride → 1-(2-Chloro-1H-indol-3-yl)ethan-1-one

HRID 1735115Notes

Reaction equation

HRID 1735115 reaction equation
O=P(Cl)(Cl)[Cl:3].[CH3:6][C:7](N(C)C)=[O:8].[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][C:13]1=O>C(Cl)(Cl)Cl>[C:7]([C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[NH:12][C:13]=1[Cl:3])(=[O:8])[CH3:6]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 31374DimethylacetamideHCID 321710Oxindole

Product 1

HCID 109323071-(2-Chloro-1H-indol-3-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

13.7 ml POCl3 was slowly added to a mixture of dimethylacetamide (5.6 ml) in 25 ml of chloroform, at 5° C. A solution of 6.66 g of oxindole in 25 ml chloroform was slowly added, and the reaction refluxed for 7 hours, and left overnight at room temperature with stirring. The reaction mixture was added to 250 ml of ice/water, the phases separated, and the organic phase extracted with water (4×50 ml). The aqueous phases were pooled and neutralized with sodium acetate, and stirred for 4 hours at room temperature. Filtration and drying gave (75). Yield 4.8 g.

Workup

  1. temperaturethe reaction refluxed for 7 hours
  2. customthe phases separated
  3. extractionthe organic phase extracted with water (4×50 ml)
  4. stirringstirred for 4 hours at room temperature
  5. filtrationFiltration
  6. customdrying

Sources & evidence

ORD record
ord-e0928d7421b54cec825ee779564cd9cb
Source dataset
uspto-grants-1996_07
Patent number
US05536721

Reaction notes

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