Hydrochloric Acid → HCID 3912385, compound

HRID 1259865Notes

Reaction equation

HRID 1259865 reaction equation
[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]2=O.[OH-:17].[K+].[C:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=O)[CH3:20].Cl>C(O)C>[C:22]1([C:19]2[CH:20]=[C:7]([C:8]([OH:17])=[O:13])[C:6]3[C:10](=[CH:11][CH:12]=[C:4]([O:3][C:2]([F:16])([F:15])[F:1])[CH:5]=3)[N:9]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7410AcetophenoneHCID 14797Potassium HydroxideHCID 27327525-(trifluoromethoxy)-2,3-dihydro-1H-indole-2,3-dione

Product 1

HCID 3912385HCID 3912385, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Commercially available 5-trifluoromethoxyisatin (5.66 g, 24.5 mmol) was added in small portions to an ethanol (75 mL) solution of potassium hydroxide (85%, 3.60 g, 54.5 mmol) under ice cooling. To the mixture, acetophenone (3.00 mL, 25.7 mmol) was further added, and then, the mixture was heated to reflux for 1 hour. After the reaction solution was concentrated, water was added to the residue, and then concentrated hydrochloric acid (4.47 mL, 53.6 mmol) was added thereto. The deposited crystal was collected by filtration, washed with water, and dried. The crude crystal was dissolved in a saturated aqueous solution of sodium bicarbonate and washed with diisopropyl ether, and then, concentrated hydrochloric acid was added until a crystal was deposited. The deposited crystal was collected by filtration, washed with water, and dried to obtain the title compound (7.06 g, 21.2 mmol) as an ocherous powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. concentrationAfter the reaction solution was concentrated
  4. additionwater was added to the residue
  5. filtrationThe deposited crystal was collected by filtration
  6. washwashed with water
  7. customdried
  8. dissolutionThe crude crystal was dissolved in a saturated aqueous solution of sodium bicarbonate
  9. washwashed with diisopropyl ether
  10. additionconcentrated hydrochloric acid was added until a crystal
  11. filtrationThe deposited crystal was collected by filtration
  12. washwashed with water
  13. customdried

Sources & evidence

ORD record
ord-d57eddcab4c244f2bdf9d02645c64bf7
Source dataset
uspto-grants-2013_06
Patent number
US08466290B2

Reaction notes

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