Sodium Hydroxide → 4-(Pyrimidin-2-yl)aniline

HRID 1767631Notes

Reaction equation

HRID 1767631 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10]([NH:13]C(=O)C(C)(C)C)=[CH:9][CH:8]=1.[OH-].[Na+]>Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22323983N-(4-(2-pyrimidinyl)phenyl)-2,2-dimethylpropanamide

Product 1

HCID 124561704-(Pyrimidin-2-yl)anilineYield 88.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

N-(4-(2-pyrimidinyl)phenyl)-2,2-dimethylpropanamide (1.41 g, 5.48 mmol) was boiled in 6 M hydrochloric acid (40 ml) for 2 h. The mixture was cooled and made strongly basic with NaOH (s) and extracted with CH2Cl2 (2×50 ml), dried (Na2SO4) and the solvent was removed in vacuo. Trituration with n-hexane gave 0.83 g (88%) of 4-(2-pyrimidinyl)aniline as a light-yellow powder. The product was further transformed by Method B and Method G (using cyclohexanecarboxaldehyde). M.p. 236–238° C.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with CH2Cl2 (2×50 ml)
  3. dry with materialdried (Na2SO4)
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-692aee8a143b474e8b523d9df24a19fa
Source dataset
uspto-grants-2007_06
Patent number
US07235548B2

Reaction notes

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