Stannous Chloride → 2-Chloro-5-methylpyridin-3-amine

HRID 602530Notes

Reaction equation

HRID 602530 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([CH3:11])=[CH:4][N:3]=1.Cl[Sn]Cl>C(O)C>[Cl:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([CH3:11])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 8183002-Chloro-5-methyl-3-nitropyridine

Product 1

HCID 27344222-Chloro-5-methylpyridin-3-amineYield 96.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
52.5 °C

Procedure

To a solution of 2-chloro-5-methyl-3-nitro-pyridine (20 g, 0.12 mol) in 300 mL of ethanol is added SnCl2 (132 g, 0.7 mol) slowly to keep internal temperature under 50° C. After addition completed, the reaction mixture is stirred for additional two hours at 50-55° C., then evaporated to dryness under reduced pressure. The residue is suspended in 400 mL of DCM, cooled with an ice bath, and neutralized carefully with 10N NaOH. The mixture is filtered through celite, washed the cake with DCM (100 mL×2). The filtrate is washed with water and brine, dried over MgSO4, and concentrated under reduced pressure to give 16.5 g of 2-chloro-5-methyl-pyridin-3-ylamine.

Workup

  1. customunder 50° C
  2. additionAfter addition
  3. customevaporated to dryness under reduced pressure
  4. temperaturecooled with an ice bath
  5. filtrationThe mixture is filtered through celite
  6. washwashed the cake with DCM (100 mL×2)
  7. washThe filtrate is washed with water and brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6db5ddb9f3e84a1b9f3a96fe0dd75996
Source dataset
uspto-grants-2011_03
Patent number
US07906528B2

Reaction notes

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