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

HRID 1472183Notes

Reaction equation

HRID 1472183 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N: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:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[C:5]=1[NH2:16])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86701070N-(2-nitro-6-(pyridin-2-yl)phenyl)acetamide

Product 1

HCID 130010352-Nitro-6-(pyridin-2-yl)anilineYield 65.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(2-nitro-6-(pyridin-2-yl)phenyl)acetamide (XCVIII) (4.41 g, 17 mmol, 1 eq) in MeOH (20 mL) was added 2N NaOH aqueous (50 mL) and the mixture was refluxed until the stirring material was consumed completely. The mixture was concentrated in vacuo to remove the MeOH and the precipitate was collected by filtration to afford 2-nitro-6-(pyridin-2-yl)aniline (XCIX) (2.4 g, 11.2 mmol, 65% yield) as a yellow solid. ESIMS found for C11H9N3O2 m/z 216 (M+H).

Workup

  1. temperaturethe mixture was refluxed until the stirring material
  2. customwas consumed completely
  3. concentrationThe mixture was concentrated in vacuo
  4. customto remove the MeOH
  5. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-be3b608a50ca4bf4b03427ec0112927a
Source dataset
uspto-grants-2015_04
Patent number
US09012472B2

Reaction notes

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