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

HRID 840548Notes

Reaction equation

HRID 840548 reaction equation
[CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][N:10]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C.Cl>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:7]2[C:2]([CH3:1])=[N:3][CH:4]=[CH:5][CH:6]=2)=[N:10][CH:11]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 106095382-Methyl-3-((5-nitropyridin-2-yl)oxy)pyridine

Product 1

HCID 108219466-[(2-Methyl-3-pyridinyl)oxy]-3-pyridinamineYield 86%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

2-(2-Methylpyridin-3-yloxy)-5-nitropyridine (D8, 81.1 g, 0.35 mole) in ethanol (2L) was treated with tin (II) chloride (232 g, 1.23 mole) in conc. hydrochloric acid (500 ml) and heated to 50° C. for 1 hour. After cooling to ambient temperature, the mixture was basified with 40% aqueous sodium hydroxide solution, extracted into ethyl acetate, dried (Na2SO4) and evaporated in vacuo to afford the title compound (60.3 g, 86%) as a brown solid.

Workup

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

Sources & evidence

ORD record
ord-e32bbe72200f4d67874d140b5ec0fea4
Source dataset
uspto-grants-2002_04
Patent number
US06369060B1

Reaction notes

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