Water → HCID 18929913, compound

HRID 3128Notes

Reaction equation

HRID 3128 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:12])[C:7](=[O:11])[NH:8]2)=[C:4]([CH2:13][CH3:14])[CH:3]=1.C1C=C([O:21]O)C(C(O)=O)=C(C(O)=O)C=1.O>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:13][CH3:14])[C:5]2[C:6](=[O:12])[O:11][C:7](=[O:21])[NH:8][C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 18929845HCID 18929845, compoundHCID 198097063-Hydroperoxyphthalic acid

Product 1

HCID 18929913HCID 18929913, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred solution of 6-bromo-4-ethyl-1H-indole-2,3-dione (2.64 g, 10.4 mM) and the hexahydrate magnesium salt of monoperoxyphthalic acid (80% pure, 3.54 g, 5.73 mM) in glacial acetic acid (30 mL) was stirred at 60° C. for 1 hr during which time a precipitate formed. The cooled reaction mixture was then poured into cold water and the resulting mixture was filtered to separate (2.04 g, 73%) the title compound as a tan solid. Recrystallization of a portion of this material from ethyl acetate/hexane provided an analytical sample of the title compound as off white crystals, mp 208.5°-210.5° C.; MS(CI): 270 (M+H).

Workup

  1. customformed
  2. customThe cooled reaction mixture
  3. filtrationthe resulting mixture was filtered
  4. customto separate (2.04 g, 73%) the title compound as a tan solid
  5. customRecrystallization of a portion of this material from ethyl acetate/hexane

Sources & evidence

ORD record
ord-212e81895b584e808d5abbbb91d99bed
Source dataset
uspto-grants-1998_03
Patent number
US05733910

Reaction notes

Loading…