Acetic Acid → HCID 54120139, compound

HRID 259938Notes

Reaction equation

HRID 259938 reaction equation
[Cl:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]2[C:5]([C:6](=[O:14])C(=O)[NH:8]2)=[C:4]([C:15]([F:18])([F:17])[F:16])[CH:3]=1.[OH-].[Na+].OO.C(O)(=[O:25])C>O>[Cl:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]([NH2:8])[C:5](=[C:4]([C:15]([F:18])([F:17])[F:16])[CH:3]=1)[C:6]([OH:14])=[O:25]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen Peroxide2×HCID 14798Sodium Hydroxide2×HCID 53812393HCID 53812393, compound

Product 1

HCID 54120139HCID 54120139, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-Chloro-7-methoxy-4-trifluoromethylisatin (13 mg, 0.046 mmol) was dissolved in NaOH (0.68M, 0.20 mL, 0.13 mmol) and H2O (0.20 mL) and then cooled to +7 C. Hydrogen peroxide (30%, 14 L, 0.14 mmol) dissolved in NaOH (0.68M, 0.49 mL, 0.33 mmol) was added dropwise during 1 min. The reaction mixture was stirred for 1 h 15 min at room temperature. Additional H2O2 (10 L) was added at 7 C. and then stirring was continued at room temperature for 2 h. Acetic acid (54 L, 0.94 mmol) was added, but no precipitation occured. Ethyl acetate (2 mL) was added and pH was raised to 6 with NaHCO3 (aq, sat.). The water phase was washed with EtOAc (3) and the combined organic layers were evaporated and co-evaporated with toluene (2). Purification by flash chromatography (SiO2, gradient EtOAc EtOAc-HOAc 100:1) yielded the title compound (5 mg). 1H NMR (CD3OD): 6.98 (s, 1H), 3.87 (s, 3H). MS (EI, 70 eV): m/z (rel. int.) 271/269 (M+, 17/48).

Workup

  1. additionwas added dropwise during 1 min
  2. stirringand then stirring
  3. waitwas continued at room temperature for 2 h
  4. customno precipitation
  5. additionEthyl acetate (2 mL) was added
  6. temperaturepH was raised to 6 with NaHCO3 (aq, sat.)
  7. washThe water phase was washed with EtOAc (3)
  8. customthe combined organic layers were evaporated
  9. customPurification by flash chromatography (SiO2, gradient EtOAc EtOAc-HOAc 100:1)

Sources & evidence

ORD record
ord-bf5f91c3bebc4f13a81089fc974e3c54
Source dataset
uspto-grants-1996_06
Patent number
US05523475

Reaction notes

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