Sodium Hydroxide → 6-Iodo-4-methylpyridin-3-amine

HRID 34066Notes

Reaction equation

HRID 34066 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-])=O)=[CH:4][N:3]=1.[OH-].[Na+]>Cl.C(OCC)C.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[I:1][C:2]1[N:3]=[CH:4][C:5]([NH2:9])=[C:6]([CH3:8])[CH:7]=1

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 230701672-Iodo-4-methyl-5-nitropyridine

Product 1

HCID 230701206-Iodo-4-methylpyridin-3-amineYield 57.5%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1.76 g of 2-iodo-4-methyl-5-nitropyridine in 7.0 mL of concentrated hydrochloric acid and 7.0 mL of diethyl ether was added 6.32 g of tin chloride (II) at room temperature, and stirred at 100° C. for 4 hours. After cooling the solution to room temperature, 5N sodium hydroxide aqueous solution was added to make the solution alkaline. Then the solution was diluted with dichloromethane and the insoluble substances were filtered off through Celite. The organic layer of the filtrate was dried over anhydrous magnesium sulfate, and the solvent was evaporated, to afford 897 mg of the title compound as orange-brown crystals.

Workup

  1. temperatureAfter cooling the solution to room temperature
  2. filtrationthe insoluble substances were filtered off through Celite
  3. dry with materialThe organic layer of the filtrate was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ea257d6261444f899590bc1ecd8b0ea9
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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