Sodium Hydroxide → HCID 178517202, compound

HRID 642052Notes

Reaction equation

HRID 642052 reaction equation
[I: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:12][NH:13][C:14]([C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=1)=[O:15].[OH-].[Na+]>C1COCC1>[I: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:12][NH:13][C:14]([C:16]1[CH:25]=[CH:24][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1)=[O:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178497994HCID 178497994, compound

Product 1

HCID 178517202HCID 178517202, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a suspension of methyl 4-{[2-(5-iodo-2-oxo-1,2-dihydro-3H-indol-3-ylidene)hydrazino]carbonyl}benzoate (80 mg, 0.18 mmol) in THF (5 mL) was added NaOH (0.2 M, 2.5 mL). The resulting solution was stirred at rt for 5 hrs and quenched with HCl (1N, 2 mL) and water (5 mL). A yellow solid precipitated out. Filtration, washing with water (2×1 mL) and drying under vacuo at rt for 72 hrs to give the tilte compound as a yellow powder (58 mg, 75%) in 98.6% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. customquenched with HCl (1N, 2 mL) and water (5 mL)
  2. customA yellow solid precipitated out
  3. filtrationFiltration
  4. washwashing with water (2×1 mL)
  5. customdrying under vacuo at rt for 72 hrs

Sources & evidence

ORD record
ord-d893d3b6c7914232a909315c62824e14
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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