Hydrogen Peroxide → 5,6-Dichloroisatoic anhydride

HRID 235287Notes

Reaction equation

HRID 235287 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:13])[C:5](=[O:12])[NH:6]2.[OH:14]O.O>C(O)(=O)C.OS(O)(=O)=O>[Cl:11][C:10]1[C:2]([Cl:1])=[C:3]2[C:4]([O:12][C:5](=[O:14])[NH:6][C:7]2=[CH:8][CH:9]=1)=[O:13]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 51399804,5-Dichloro-1H-indole-2,3-dione

Product 1

HCID 541214315,6-Dichloroisatoic anhydrideYield 90%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 4,5-dichloroisatin (13f, 216 mg, 1.0 mmol) in glacial acetic acid (5 mL) and 2 drops (about 0.02 mL) of conc H2SO4 was added 0.34 mL (about 3 mmol) of 30% H2O2. The mixture was stirred at 70° C. (bath) for 2.5 h (the mixture turned into a solution, then formed a precipitate), allowed to cool to 22° C. and cold water (10 mL) was added. The precipitate was filtered, washed with water (6×10 mL), dried to give 208 mg (90%) of 14e as an orange-yellow powder, mp 267°-9° C. (dec). IR, 1810, 1779, 1762, 1711, 1600, 1335, 1254, 1041, 1024 cm-1 ; 1H NMR δ 11.952 (bs, 1H), 7.928 (d, J=8.7 Hz, 1H), 7.110 (d, J=8.7Hz, 1H); HRMS Calcd for C8H3Cl2NO3 : 230.9490; Found: 230.9489.

Workup

  1. customformed a precipitate),
  2. temperatureto cool to 22° C.
  3. filtrationThe precipitate was filtered
  4. washwashed with water (6×10 mL)
  5. customdried

Sources & evidence

ORD record
ord-b3627186efc645b3bd69ec08b71e16f0
Source dataset
uspto-grants-1997_01
Patent number
US05597922

Reaction notes

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