Water → HCID 10702137, compound

HRID 2102976Notes

Reaction equation

HRID 2102976 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([N+:15]([O-])=O)=[CH:10][CH:9]=2)=O)C.[AlH4-].[Li+].O.[OH-].[Na+]>C1COCC1>[NH2:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:4][OH:3])=[CH:14]2

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 28112Lithium aluminum hydrideHCID 280312Ethyl 5-nitro-1H-indole-2-carboxylate

Product 1

HCID 10702137HCID 10702137, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Ethoxycarbonyl-5-nitroindole (500 mg, 0.002 mol) was dissolved in 50 mL THF, added lithium tetrahydroaluminate (341 mg, 0.00898 mol) portionwise and stirred at room temperature overnight. Water (341 μL), 15% NaOH solution (341 μL), and water (1.1 mL) were added cautiously and the mixtured was filtered. The filtrate was concentrated under vacuum to give the product (300 mg, 98%) as an oil. m/z=162.9.

Workup

  1. filtrationthe mixtured was filtered
  2. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-3cf161f2d3504d1f9930a38482aa5a71
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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