Sodium Hydroxide → 6-[(Pyridin-2-yl)methoxy]pyridin-3-amine

HRID 427722Notes

Reaction equation

HRID 427722 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[N:8][CH:9]=1)([O-])=O.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C.Cl.O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[N:8][CH:9]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 183577252-(Pyridin-2-ylmethoxy)-5-nitropyridine

Product 1

HCID 154477886-[(Pyridin-2-yl)methoxy]pyridin-3-amineYield 78%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

5-Nitro-2-(pyridin-2-ylmethyloxy)pyridine (D1, 2.0 g, 0.0087 mole) in ethanol (70 ml) was treated with tin (II) chloride (8.3 g, 0.044 mole) in conc. HCl (15 ml). The mixture was heated to 50° C. for 0.5 hour. After cooling to room temperature, the mixture was diluted with water, basified with 10% aqueous sodium hydroxide solution, extracted into ethyl acetate, dried (Na2SO4) and evaporated in vacuo to afford the title compound (1.36 g, 78%) as a brown oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted into ethyl acetate
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-19bdabcaa6ba44608332a5b83fb7d5f1
Source dataset
uspto-grants-2001_11
Patent number
US06313145B1

Reaction notes

Loading…