Acetic Anhydride → HCID 21862569, compound

HRID 239006Notes

Reaction equation

HRID 239006 reaction equation
C([CH2:4][NH:5][C:6]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:7]=1[C:8](O)=O)(O)=O.[C:16]([O-:19])(=[O:18])[CH3:17].[Na+].C(O[C:25](=[O:27])[CH3:26])(=O)C>>[C:25]([N:5]1[C:6]2[C:7](=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=2)[C:8]([O:18][C:16](=[O:19])[CH3:17])=[CH:4]1)(=[O:27])[CH3:26]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 14859098HCID 14859098, compound

Product 1

HCID 21862569HCID 21862569, compoundYield 64%

Conditions

Temperature
60 °C

Procedure

2-(N-carboxymethylamino)-5-chlorobenzoic acid (1.20 g, 5.2 mmol) and anhydrous sodium acetate (0.6 g, 7.3 mmol) were dissolved in 8 ml acetic anhydride. After stirred for 5 hours at 60° C., the reaction mixture was cooled down to room temperature, and the sodium acetate was filtered off. The filtrate was concentrated, and the residue was dissolved in 100 ml ethyl acetate. 100 ml water and 20 ml saturated sodium bicarbonate were added to the solution, and the organic layer was separated. The aqueous layer was extracted with ethyl acetate (50 ml×2). The combined organic phases were washed with saturated sodium bicarbonate (100 ml×2), dried, and evaporated, to obtain a white solid (1-acetyl-5-chloro-3-acetoxyindole) (0.84 g, yield: 64%).

Workup

  1. temperaturethe reaction mixture was cooled down to room temperature
  2. filtrationthe sodium acetate was filtered off
  3. concentrationThe filtrate was concentrated
  4. dissolutionthe residue was dissolved in 100 ml ethyl acetate
  5. addition100 ml water and 20 ml saturated sodium bicarbonate were added to the solution
  6. customthe organic layer was separated
  7. extractionThe aqueous layer was extracted with ethyl acetate (50 ml×2)
  8. washThe combined organic phases were washed with saturated sodium bicarbonate (100 ml×2)
  9. customdried
  10. customevaporated

Sources & evidence

ORD record
ord-35b01cf346aa4e3a94d2da9bf9133673
Source dataset
uspto-grants-2014_02
Patent number
US08642765B2

Reaction notes

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