Sodium Hydroxide → 6-[(2-Methyl-3-pyridinyl)oxy]-3-pyridinamine

HRID 1281172Notes

Reaction equation

HRID 1281172 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[CH3:6][C:7]1[C:12]([O:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][N:15]=2)=[CH:11][CH:10]=[CH:9][N:8]=1.[OH-].[Na+]>Cl>[CH3:6][C:7]1[C:12]([O:13][C:14]2[N:15]=[CH:16][C:17]([NH2:20])=[CH:18][CH:19]=2)=[CH:11][CH:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 106095382-Methyl-3-((5-nitropyridin-2-yl)oxy)pyridine

Product 1

HCID 108219466-[(2-Methyl-3-pyridinyl)oxy]-3-pyridinamine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 14.35 g of tin chloride in 30 ml of concentrated hydrochloric acid is added to a mixture of 5 g of 2-(2-methylpyrid-3-yloxy)-5-nitropyridine and the whole is heated at reflux for 1 hour. The reaction mixture is cooled and adjusted to basic pH by the addition of concentrated sodium hydroxide solution. After the removal of a precipitate by filtration, the aqueous phase is extracted with ethyl acetate. After conventional working up, the expected product is isolated in the form of a violet powder.

Workup

  1. temperaturethe whole is heated
  2. temperatureat reflux for 1 hour
  3. temperatureThe reaction mixture is cooled
  4. customAfter the removal of a precipitate
  5. filtrationby filtration
  6. extractionthe aqueous phase is extracted with ethyl acetate

Sources & evidence

ORD record
ord-0f2547170e994af8a5e1e05d8b793228
Source dataset
uspto-grants-2002_09
Patent number
US06452015B2

Reaction notes

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