Sodium Hydroxide → 2-Nitro-6-(pyridin-4-yl)aniline

HRID 1916484Notes

Reaction equation

HRID 1916484 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[C:5]=1[NH:16]C(=O)C)([O-:3])=[O:2].[OH-].[Na+]>CO>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=2)[C:5]=1[NH2:16])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86701067N-(2-nitro-6-(pyridin-4-yl)phenyl)acetamide

Product 1

HCID 867010682-Nitro-6-(pyridin-4-yl)anilineYield 92.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(2-nitro-6-(pyridin-4-yl)phenyl)acetamide (XCIII) (3.94 g, 15 mmol, 1 eq) in methanol (20 mL) was added 2 N aqueous NaOH solution (50 mL) and the mixture was refluxed until the starting material was consumed completely, the precipitate was collected by filtration to afford the 2-nitro-6-(pyridin-4-yl)aniline (XCIV) (3.0 g, 13.9 mmol, 91% yield) as yellow solid. ESIMS found for C11H9N3O2 m/z 216 (M+H).

Workup

  1. temperaturethe mixture was refluxed until the starting material
  2. customwas consumed completely
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-4ef726c0f3e549628654c0ba68d830ad
Source dataset
uspto-grants-2013_12
Patent number
US08618128B1

Reaction notes

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