5-Bromoisatin → HCID 178520470, compound

HRID 642125Notes

Reaction equation

HRID 642125 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[NH:13]([C:15](=[O:28])[CH2:16][CH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([NH:24][NH2:25])=[O:23])=[CH:20][CH:19]=1)[NH2:14]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[N:25][NH:24][C:22](=[O:23])[C:21]1[CH:26]=[CH:27][C:18]([CH2:17][CH2:16][C:15]([NH:13][N:14]=[C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=3)[NH:7][C:6]2=[O:11])=[O:28])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 68895-BromoisatinHCID 684097474-(3-Hydrazino-3-oxopropyl)benzohydrazide

Product 1

HCID 178520470HCID 178520470, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 5-bromo-1H-indole-2,3-dione (67 mg, 0.30 mmol and) and 4-(3-hydrazino-3-oxopropyl)benzohydrazide (0.03 mg, 0.13 mmol) in acetic acid (2 mL) was heated at 100° C. for 80 min. The reaction mixture was cooled to rt and a yellow solid precipitated out. Filtration, washing with AcOH (3×1 mL) and with AcOH/water (2×1 mL) and water (3×1 mL) and drying in vacuo at 70° C. for 4 hrs gave 68 mg of the title compound in a 79% yield as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. customa yellow solid precipitated out
  3. filtrationFiltration
  4. washwashing with AcOH (3×1 mL) and with AcOH/water (2×1 mL) and water (3×1 mL)
  5. customdrying in vacuo at 70° C. for 4 hrs

Sources & evidence

ORD record
ord-4384265fb4ae4b1bbd486c3aca47b108
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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