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

HRID 218470Notes

Reaction equation

HRID 218470 reaction equation
Cl[Sn]Cl.O.[I:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([N+:13]([O-])=O)=[CH:8][N:7]=1.[OH-].[Na+]>CCOC(C)=O>[I:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([NH2:13])=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 230701672-Iodo-4-methyl-5-nitropyridineHCID 43835034Tin dichloride dihydrate

Product 1

HCID 230701206-Iodo-4-methylpyridin-3-amineYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of SnCl2.H2O (20.5 g, 108 mmol) in EtOAc (200 mL) was added 2-iodo-4-methyl-5-nitropyridine (5.7 g, 21.6 mmol) in EtOAc (20 mL). Heat was released, and the reaction mixture was kept at reflux for 2 hr. After cooling to rt, the reaction mixture was treated with 50% NaOH (50 mL). Solid was filtered off and washed with EtOAc. The filtrate was washed with brine, dried, and concentrated to afford 2-iodo-4-methyl-5-pyridinamine (5 g, 99%) as a yellow solid.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 2 hr
  3. filtrationSolid was filtered off
  4. washwashed with EtOAc
  5. washThe filtrate was washed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bbbbf47f9c13471fbab8bdaeb0ef81e0
Source dataset
uspto-grants-2012_06
Patent number
US08198456B2

Reaction notes

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