Water → HCID 178507313, compound

HRID 2102958Notes

Reaction equation

HRID 2102958 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH:13]=[O:14])=[N:9][NH:10]2)=[CH:6][CH:5]=1)([O-])=O.[AlH4-].[Li+].O.[OH-].[Na+]>C1COCC1>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH2:13][OH:14])=[N:9][NH:10]2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 28112Lithium aluminum hydrideHCID 178520046HCID 178520046, compound

Product 1

HCID 178507313HCID 178507313, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-nitro-1H-indazole-3-carbaldehyde (500 mg, 0.003 mol) was dissolved in 50 mL THF. Lithium tetrahydroaluminate (400 mg, 0.01 mol) was added in 3 portions and the reaction mixture was stirred at room temperature overnight. Water (400 μL), 15% NaOH solution (400 μL), then water (1.2 mL) was added, and then the crystalline brown-yellow precipitate was filtered off. The filtrate was concentrate to an oil which was used directly in the next step without further purification. m/z=164.0. 1H NMR (d4-MeOH) δ 7.2 (1H, d), 7.05 (1H, d), 6.85 (1H, dd), 4.74 (2H, s).

Workup

  1. filtrationthe crystalline brown-yellow precipitate was filtered off
  2. concentrationThe filtrate was concentrate to an oil which
  3. customwas used directly in the next step without further purification

Sources & evidence

ORD record
ord-8d0c25dbbb3047789475244a69da3b68
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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