Sodium Hydroxide → 5-Amino-3-methyl-2(pyridin-2-ylmethyloxy)pyridine

HRID 427734Notes

Reaction equation

HRID 427734 reaction equation
[CH3:1][C:2]1[C:3]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[N:4][CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C.Cl.O>[NH2:8][C:6]1[CH:7]=[C:2]([CH3:1])[C:3]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[N:4][CH:5]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 18357727HCID 18357727, compound

Product 1

HCID 183577225-Amino-3-methyl-2(pyridin-2-ylmethyloxy)pyridineYield 100%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

3-Methyl-5-nitro-2-(pyridin-2-ylmethyloxy)pyridine (D14, 1.42 g, 5.8 mmol) in ethanol (100 ml) was treated dropwise with a solution of tin (II) chloride (5.68 g) in conc. HCl (10 ml) at 60° C. The mixture was stirred at 60° C. for one hour, then cooled, diluted with water and basified with 40% aqueous sodium hydroxide solution. The aqueous solution was extracted with dichloromethane (3×100 ml), dried (Na2SO4) and evaporated in vacuo to afford the title compound (1.24 g, 100%) as a brown liquid.

Workup

  1. temperaturecooled
  2. extractionThe aqueous solution was extracted with dichloromethane (3×100 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-2104a3e6c5d6496da2e7bb52abd4c8e7
Source dataset
uspto-grants-2001_11
Patent number
US06313145B1

Reaction notes

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