Acetic Anhydride → HCID 58031721, compound

HRID 40481Notes

Reaction equation

HRID 40481 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:11]=[CH:10][C:9]2[C:5](=[CH:6][C:7](=[O:12])[N:8]=2)[CH:4]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16]>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C>[C:15]([N:8]1[C:9]2[C:5](=[CH:4][C:3]([C:2]([F:1])([F:13])[F:14])=[CH:11][CH:10]=2)[CH2:6][C:7]1=[O:12])(=[O:17])[CH3:16]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 467398615-Trifluoromethyloxoindole

Product 1

HCID 58031721HCID 58031721, compound

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.0 g of 5-trifluoromethyloxoindole were dissolved in 25 ml of xylene, 2.41 ml of acetic anhydride were added and the mixture was heated to boiling under reflux for 5 hours. The reaction solution was cooled to room temperature and diluted with 150 ml of ethyl acetate, and washed with 80 ml each of water, saturated sodium bicarbonate solution and saturated NaCl solution. The organic phase was dried over MgSO4 and concentrated under reduced pressure. The residue was purified on silica gel with the eluent n-heptane=>n-heptane/ethyl acetate=3:1. This gave 1.74 g of 1-acetyl-5-trifluoromethyl-1,3-dihydroindol-2-one as a colorless solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. washwashed with 80 ml each of water, saturated sodium bicarbonate solution and saturated NaCl solution
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified on silica gel with the eluent n-heptane=>n-heptane/ethyl acetate=3:1

Sources & evidence

ORD record
ord-2e33e3dec69a4be8869a3b0ce689dbfe
Source dataset
uspto-grants-2013_09
Patent number
US08530413B2

Reaction notes

Loading…